diff --git a/apps/marketing/src/app/(marketing)/singleplayer/client.tsx b/apps/marketing/src/app/(marketing)/singleplayer/client.tsx
index 7fe3297ee..2d8bbe9d9 100644
--- a/apps/marketing/src/app/(marketing)/singleplayer/client.tsx
+++ b/apps/marketing/src/app/(marketing)/singleplayer/client.tsx
@@ -98,6 +98,7 @@ export const SinglePlayerClient = () => {
         height: new Prisma.Decimal(field.pageHeight),
         customText: '',
         inserted: false,
+        fieldMeta: field.fieldMeta ?? {},
       })),
     );
 
@@ -131,7 +132,9 @@ export const SinglePlayerClient = () => {
           positionY: field.positionY.toNumber(),
           width: field.width.toNumber(),
           height: field.height.toNumber(),
+          fieldMeta: field.fieldMeta,
         })),
+        fieldMeta: { type: undefined },
       });
 
       analytics.capture('Marketing: SPM - Document signed', {
diff --git a/apps/web/src/app/(dashboard)/documents/[id]/edit-document.tsx b/apps/web/src/app/(dashboard)/documents/[id]/edit-document.tsx
index 6d9ac219f..cd4b133d4 100644
--- a/apps/web/src/app/(dashboard)/documents/[id]/edit-document.tsx
+++ b/apps/web/src/app/(dashboard)/documents/[id]/edit-document.tsx
@@ -232,6 +232,14 @@ export const EditDocumentForm = ({
         fields: data.fields,
       });
 
+      // Clear all field data from localStorage
+      for (let i = 0; i < localStorage.length; i++) {
+        const key = localStorage.key(i);
+        if (key && key.startsWith('field_')) {
+          localStorage.removeItem(key);
+        }
+      }
+
       // Router refresh is here to clear the router cache for when navigating to /documents.
       router.refresh();
 
@@ -241,7 +249,7 @@ export const EditDocumentForm = ({
 
       toast({
         title: 'Error',
-        description: 'An error occurred while adding signers.',
+        description: 'An error occurred while adding the fields.',
         variant: 'destructive',
       });
     }
@@ -351,6 +359,7 @@ export const EditDocumentForm = ({
               fields={fields}
               onSubmit={onAddFieldsFormSubmit}
               isDocumentPdfLoaded={isDocumentPdfLoaded}
+              teamId={team?.id}
             />
 
             <AddSubjectFormPartial
diff --git a/apps/web/src/app/(dashboard)/documents/_action-items/resend-document.tsx b/apps/web/src/app/(dashboard)/documents/_action-items/resend-document.tsx
index 5bfd85645..f84ca6997 100644
--- a/apps/web/src/app/(dashboard)/documents/_action-items/resend-document.tsx
+++ b/apps/web/src/app/(dashboard)/documents/_action-items/resend-document.tsx
@@ -150,7 +150,7 @@ export const ResendDocumentActionItem = ({
 
                       <FormControl>
                         <Checkbox
-                          className="h-5 w-5 rounded-full data-[state=checked]:border-black data-[state=checked]:bg-black "
+                          className="h-5 w-5 rounded-full data-[state=checked]:border-black data-[state=checked]:bg-black"
                           checkClassName="text-white"
                           value={recipient.id}
                           checked={value.includes(recipient.id)}
diff --git a/apps/web/src/app/(dashboard)/templates/[id]/edit-template.tsx b/apps/web/src/app/(dashboard)/templates/[id]/edit-template.tsx
index cf137152e..f53c2a795 100644
--- a/apps/web/src/app/(dashboard)/templates/[id]/edit-template.tsx
+++ b/apps/web/src/app/(dashboard)/templates/[id]/edit-template.tsx
@@ -12,10 +12,7 @@ import type { TemplateWithDetails } from '@documenso/prisma/types/template';
 import { trpc } from '@documenso/trpc/react';
 import { cn } from '@documenso/ui/lib/utils';
 import { Card, CardContent } from '@documenso/ui/primitives/card';
-import {
-  DocumentFlowFormContainer,
-  DocumentFlowFormContainerHeader,
-} from '@documenso/ui/primitives/document-flow/document-flow-root';
+import { DocumentFlowFormContainer } from '@documenso/ui/primitives/document-flow/document-flow-root';
 import type { DocumentFlowStep } from '@documenso/ui/primitives/document-flow/types';
 import { LazyPDFViewer } from '@documenso/ui/primitives/lazy-pdf-viewer';
 import { Stepper } from '@documenso/ui/primitives/stepper';
@@ -184,6 +181,14 @@ export const EditTemplateForm = ({
         fields: data.fields,
       });
 
+      // Clear all field data from localStorage
+      for (let i = 0; i < localStorage.length; i++) {
+        const key = localStorage.key(i);
+        if (key && key.startsWith('field_')) {
+          localStorage.removeItem(key);
+        }
+      }
+
       toast({
         title: 'Template saved',
         description: 'Your templates has been saved successfully.',
@@ -232,11 +237,6 @@ export const EditTemplateForm = ({
           className="lg:h-[calc(100vh-6rem)]"
           onSubmit={(e) => e.preventDefault()}
         >
-          <DocumentFlowFormContainerHeader
-            title={currentDocumentFlow.title}
-            description={currentDocumentFlow.description}
-          />
-
           <Stepper
             currentStep={currentDocumentFlow.stepIndex}
             setCurrentStep={(step) => setStep(EditTemplateSteps[step - 1])}
@@ -269,6 +269,7 @@ export const EditTemplateForm = ({
               recipients={recipients}
               fields={fields}
               onSubmit={onAddFieldsFormSubmit}
+              teamId={team?.id}
             />
           </Stepper>
         </DocumentFlowFormContainer>
diff --git a/apps/web/src/app/(recipient)/d/[token]/sign-direct-template.tsx b/apps/web/src/app/(recipient)/d/[token]/sign-direct-template.tsx
index 1531b6969..47719014b 100644
--- a/apps/web/src/app/(recipient)/d/[token]/sign-direct-template.tsx
+++ b/apps/web/src/app/(recipient)/d/[token]/sign-direct-template.tsx
@@ -6,6 +6,13 @@ import { match } from 'ts-pattern';
 import { DEFAULT_DOCUMENT_DATE_FORMAT } from '@documenso/lib/constants/date-formats';
 import { PDF_VIEWER_PAGE_SELECTOR } from '@documenso/lib/constants/pdf-viewer';
 import { DEFAULT_DOCUMENT_TIME_ZONE } from '@documenso/lib/constants/time-zones';
+import {
+  ZCheckboxFieldMeta,
+  ZDropdownFieldMeta,
+  ZNumberFieldMeta,
+  ZRadioFieldMeta,
+  ZTextFieldMeta,
+} from '@documenso/lib/types/field-meta';
 import { sortFieldsByPosition, validateFieldsInserted } from '@documenso/lib/utils/fields';
 import type { Field, Recipient, Signature } from '@documenso/prisma/client';
 import { FieldType } from '@documenso/prisma/client';
@@ -30,10 +37,14 @@ import { Label } from '@documenso/ui/primitives/label';
 import { SignaturePad } from '@documenso/ui/primitives/signature-pad';
 import { useStep } from '@documenso/ui/primitives/stepper';
 
+import { CheckboxField } from '~/app/(signing)/sign/[token]/checkbox-field';
 import { DateField } from '~/app/(signing)/sign/[token]/date-field';
+import { DropdownField } from '~/app/(signing)/sign/[token]/dropdown-field';
 import { EmailField } from '~/app/(signing)/sign/[token]/email-field';
 import { NameField } from '~/app/(signing)/sign/[token]/name-field';
+import { NumberField } from '~/app/(signing)/sign/[token]/number-field';
 import { useRequiredSigningContext } from '~/app/(signing)/sign/[token]/provider';
+import { RadioField } from '~/app/(signing)/sign/[token]/radio-field';
 import { SignDialog } from '~/app/(signing)/sign/[token]/sign-dialog';
 import { SignatureField } from '~/app/(signing)/sign/[token]/signature-field';
 import { TextField } from '~/app/(signing)/sign/[token]/text-field';
@@ -200,15 +211,96 @@ export const SignDirectTemplateForm = ({
                   onUnsignField={onUnsignField}
                 />
               ))
-              .with(FieldType.TEXT, () => (
-                <TextField
-                  key={field.id}
-                  field={field}
-                  recipient={directRecipient}
-                  onSignField={onSignField}
-                  onUnsignField={onUnsignField}
-                />
-              ))
+              .with(FieldType.TEXT, () => {
+                const parsedFieldMeta = field.fieldMeta
+                  ? ZTextFieldMeta.parse(field.fieldMeta)
+                  : null;
+
+                return (
+                  <TextField
+                    key={field.id}
+                    field={{
+                      ...field,
+                      fieldMeta: parsedFieldMeta,
+                    }}
+                    recipient={directRecipient}
+                    onSignField={onSignField}
+                    onUnsignField={onUnsignField}
+                  />
+                );
+              })
+              .with(FieldType.NUMBER, () => {
+                const parsedFieldMeta = field.fieldMeta
+                  ? ZNumberFieldMeta.parse(field.fieldMeta)
+                  : null;
+
+                return (
+                  <NumberField
+                    key={field.id}
+                    field={{
+                      ...field,
+                      fieldMeta: parsedFieldMeta,
+                    }}
+                    recipient={directRecipient}
+                    onSignField={onSignField}
+                    onUnsignField={onUnsignField}
+                  />
+                );
+              })
+              .with(FieldType.DROPDOWN, () => {
+                const parsedFieldMeta = field.fieldMeta
+                  ? ZDropdownFieldMeta.parse(field.fieldMeta)
+                  : null;
+
+                return (
+                  <DropdownField
+                    key={field.id}
+                    field={{
+                      ...field,
+                      fieldMeta: parsedFieldMeta,
+                    }}
+                    recipient={directRecipient}
+                    onSignField={onSignField}
+                    onUnsignField={onUnsignField}
+                  />
+                );
+              })
+              .with(FieldType.RADIO, () => {
+                const parsedFieldMeta = field.fieldMeta
+                  ? ZRadioFieldMeta.parse(field.fieldMeta)
+                  : null;
+
+                return (
+                  <RadioField
+                    key={field.id}
+                    field={{
+                      ...field,
+                      fieldMeta: parsedFieldMeta,
+                    }}
+                    recipient={directRecipient}
+                    onSignField={onSignField}
+                    onUnsignField={onUnsignField}
+                  />
+                );
+              })
+              .with(FieldType.CHECKBOX, () => {
+                const parsedFieldMeta = field.fieldMeta
+                  ? ZCheckboxFieldMeta.parse(field.fieldMeta)
+                  : null;
+
+                return (
+                  <CheckboxField
+                    key={field.id}
+                    field={{
+                      ...field,
+                      fieldMeta: parsedFieldMeta,
+                    }}
+                    recipient={directRecipient}
+                    onSignField={onSignField}
+                    onUnsignField={onUnsignField}
+                  />
+                );
+              })
               .otherwise(() => null),
           )}
         </ElementVisible>
diff --git a/apps/web/src/app/(signing)/sign/[token]/checkbox-field.tsx b/apps/web/src/app/(signing)/sign/[token]/checkbox-field.tsx
new file mode 100644
index 000000000..8f5e3b339
--- /dev/null
+++ b/apps/web/src/app/(signing)/sign/[token]/checkbox-field.tsx
@@ -0,0 +1,292 @@
+'use client';
+
+import { useEffect, useMemo, useState, useTransition } from 'react';
+
+import { useRouter } from 'next/navigation';
+
+import { Loader } from 'lucide-react';
+
+import { DO_NOT_INVALIDATE_QUERY_ON_MUTATION } from '@documenso/lib/constants/trpc';
+import { AppError, AppErrorCode } from '@documenso/lib/errors/app-error';
+import type { TRecipientActionAuth } from '@documenso/lib/types/document-auth';
+import { ZCheckboxFieldMeta } from '@documenso/lib/types/field-meta';
+import type { Recipient } from '@documenso/prisma/client';
+import type { FieldWithSignatureAndFieldMeta } from '@documenso/prisma/types/field-with-signature-and-fieldmeta';
+import { trpc } from '@documenso/trpc/react';
+import type {
+  TRemovedSignedFieldWithTokenMutationSchema,
+  TSignFieldWithTokenMutationSchema,
+} from '@documenso/trpc/server/field-router/schema';
+import { FieldToolTip } from '@documenso/ui/components/field/field-tooltip';
+import { Checkbox } from '@documenso/ui/primitives/checkbox';
+import { checkboxValidationSigns } from '@documenso/ui/primitives/document-flow/field-items-advanced-settings/constants';
+import { Label } from '@documenso/ui/primitives/label';
+import { useToast } from '@documenso/ui/primitives/use-toast';
+
+import { useRequiredDocumentAuthContext } from './document-auth-provider';
+import { SigningFieldContainer } from './signing-field-container';
+
+export type CheckboxFieldProps = {
+  field: FieldWithSignatureAndFieldMeta;
+  recipient: Recipient;
+  onSignField?: (value: TSignFieldWithTokenMutationSchema) => Promise<void> | void;
+  onUnsignField?: (value: TRemovedSignedFieldWithTokenMutationSchema) => Promise<void> | void;
+};
+
+export const CheckboxField = ({
+  field,
+  recipient,
+  onSignField,
+  onUnsignField,
+}: CheckboxFieldProps) => {
+  const router = useRouter();
+  const { toast } = useToast();
+  const [isPending, startTransition] = useTransition();
+  const { executeActionAuthProcedure } = useRequiredDocumentAuthContext();
+
+  const parsedFieldMeta = ZCheckboxFieldMeta.parse(field.fieldMeta);
+
+  const values = parsedFieldMeta.values?.map((item) => ({
+    ...item,
+    value: item.value.length > 0 ? item.value : `empty-value-${item.id}`,
+  }));
+  const [checkedValues, setCheckedValues] = useState(
+    values
+      ?.map((item) =>
+        item.checked ? (item.value.length > 0 ? item.value : `empty-value-${item.id}`) : '',
+      )
+      .filter(Boolean) || [],
+  );
+
+  const isReadOnly = parsedFieldMeta.readOnly;
+
+  const checkboxValidationRule = parsedFieldMeta.validationRule;
+  const checkboxValidationLength = parsedFieldMeta.validationLength;
+  const validationSign = checkboxValidationSigns.find(
+    (sign) => sign.label === checkboxValidationRule,
+  );
+
+  const isLengthConditionMet = useMemo(() => {
+    if (!validationSign) return true;
+    return (
+      (validationSign.value === '>=' && checkedValues.length >= (checkboxValidationLength || 0)) ||
+      (validationSign.value === '=' && checkedValues.length === (checkboxValidationLength || 0)) ||
+      (validationSign.value === '<=' && checkedValues.length <= (checkboxValidationLength || 0))
+    );
+  }, [checkedValues, validationSign, checkboxValidationLength]);
+
+  const { mutateAsync: signFieldWithToken, isLoading: isSignFieldWithTokenLoading } =
+    trpc.field.signFieldWithToken.useMutation(DO_NOT_INVALIDATE_QUERY_ON_MUTATION);
+
+  const {
+    mutateAsync: removeSignedFieldWithToken,
+    isLoading: isRemoveSignedFieldWithTokenLoading,
+  } = trpc.field.removeSignedFieldWithToken.useMutation(DO_NOT_INVALIDATE_QUERY_ON_MUTATION);
+
+  const isLoading = isSignFieldWithTokenLoading || isRemoveSignedFieldWithTokenLoading || isPending;
+  const shouldAutoSignField =
+    (!field.inserted && checkedValues.length > 0 && isLengthConditionMet) ||
+    (!field.inserted && isReadOnly && isLengthConditionMet);
+
+  const onSign = async (authOptions?: TRecipientActionAuth) => {
+    try {
+      const payload: TSignFieldWithTokenMutationSchema = {
+        token: recipient.token,
+        fieldId: field.id,
+        value: checkedValues.join(','),
+        isBase64: true,
+        authOptions,
+      };
+
+      if (onSignField) {
+        await onSignField(payload);
+      } else {
+        await signFieldWithToken(payload);
+      }
+
+      startTransition(() => router.refresh());
+    } catch (err) {
+      const error = AppError.parseError(err);
+
+      if (error.code === AppErrorCode.UNAUTHORIZED) {
+        throw error;
+      }
+
+      console.error(err);
+
+      toast({
+        title: 'Error',
+        description: 'An error occurred while signing the document.',
+        variant: 'destructive',
+      });
+    }
+  };
+
+  const onRemove = async (fieldType?: string) => {
+    try {
+      const payload: TRemovedSignedFieldWithTokenMutationSchema = {
+        token: recipient.token,
+        fieldId: field.id,
+      };
+
+      if (onUnsignField) {
+        await onUnsignField(payload);
+      } else {
+        await removeSignedFieldWithToken(payload);
+      }
+
+      if (fieldType === 'Checkbox') {
+        setCheckedValues([]);
+      }
+
+      startTransition(() => router.refresh());
+    } catch (err) {
+      console.error(err);
+
+      toast({
+        title: 'Error',
+        description: 'An error occurred while removing the signature.',
+        variant: 'destructive',
+      });
+    }
+  };
+
+  const handleCheckboxChange = (value: string, itemId: number) => {
+    const updatedValue = value || `empty-value-${itemId}`;
+    const updatedValues = checkedValues.includes(updatedValue)
+      ? checkedValues.filter((v) => v !== updatedValue)
+      : [...checkedValues, updatedValue];
+
+    setCheckedValues(updatedValues);
+  };
+
+  const handleCheckboxOptionClick = async (item: {
+    id: number;
+    checked: boolean;
+    value: string;
+  }) => {
+    let updatedValues: string[] = [];
+
+    try {
+      const isChecked = checkedValues.includes(
+        item.value.length > 0 ? item.value : `empty-value-${item.id}`,
+      );
+
+      if (!isChecked) {
+        updatedValues = [
+          ...checkedValues,
+          item.value.length > 0 ? item.value : `empty-value-${item.id}`,
+        ];
+
+        await removeSignedFieldWithToken({
+          token: recipient.token,
+          fieldId: field.id,
+        });
+
+        if (isLengthConditionMet) {
+          await signFieldWithToken({
+            token: recipient.token,
+            fieldId: field.id,
+            value: updatedValues.join(','),
+            isBase64: true,
+          });
+        }
+      } else {
+        updatedValues = checkedValues.filter(
+          (v) => v !== item.value && v !== `empty-value-${item.id}`,
+        );
+
+        await removeSignedFieldWithToken({
+          token: recipient.token,
+          fieldId: field.id,
+        });
+      }
+    } catch (err) {
+      console.error(err);
+
+      toast({
+        title: 'Error',
+        description: 'An error occurred while updating the signature.',
+        variant: 'destructive',
+      });
+    } finally {
+      setCheckedValues(updatedValues);
+      startTransition(() => router.refresh());
+    }
+  };
+
+  useEffect(() => {
+    if (shouldAutoSignField) {
+      void executeActionAuthProcedure({
+        onReauthFormSubmit: async (authOptions) => await onSign(authOptions),
+        actionTarget: field.type,
+      });
+    }
+  }, [checkedValues, isLengthConditionMet, field.inserted]);
+
+  return (
+    <SigningFieldContainer field={field} onSign={onSign} onRemove={onRemove} type="Checkbox">
+      {isLoading && (
+        <div className="bg-background absolute inset-0 z-20 flex items-center justify-center rounded-md">
+          <Loader className="text-primary h-5 w-5 animate-spin md:h-8 md:w-8" />
+        </div>
+      )}
+
+      {!field.inserted && (
+        <>
+          {!isLengthConditionMet && (
+            <FieldToolTip key={field.id} field={field} color="warning" className="">
+              {validationSign?.label} {checkboxValidationLength}
+            </FieldToolTip>
+          )}
+          <div className="z-50 flex flex-col gap-y-2">
+            {values?.map((item: { id: number; value: string; checked: boolean }, index: number) => {
+              const itemValue = item.value || `empty-value-${item.id}`;
+
+              return (
+                <div key={index} className="flex items-center gap-x-1.5">
+                  <Checkbox
+                    className="h-4 w-4"
+                    checkClassName="text-white"
+                    id={`checkbox-${index}`}
+                    checked={checkedValues.includes(itemValue)}
+                    onCheckedChange={() => handleCheckboxChange(item.value, item.id)}
+                  />
+                  <Label htmlFor={`checkbox-${index}`}>
+                    {item.value.includes('empty-value-') ? '' : item.value}
+                  </Label>
+                </div>
+              );
+            })}
+          </div>
+        </>
+      )}
+
+      {field.inserted && (
+        <div className="flex flex-col gap-y-2">
+          {values?.map((item: { id: number; value: string; checked: boolean }, index: number) => {
+            const itemValue = item.value || `empty-value-${item.id}`;
+
+            return (
+              <div key={index} className="flex items-center gap-x-1.5">
+                <Checkbox
+                  className="h-4 w-4"
+                  checkClassName="text-white"
+                  id={`checkbox-${index}`}
+                  checked={field.customText
+                    .split(',')
+                    .some((customValue) => customValue === itemValue)}
+                  disabled={isLoading}
+                  onCheckedChange={() => void handleCheckboxOptionClick(item)}
+                />
+                <Label htmlFor={`checkbox-${index}`}>
+                  {item.value.includes('empty-value-') ? '' : item.value}
+                </Label>
+              </div>
+            );
+          })}
+        </div>
+      )}
+    </SigningFieldContainer>
+  );
+};
diff --git a/apps/web/src/app/(signing)/sign/[token]/date-field.tsx b/apps/web/src/app/(signing)/sign/[token]/date-field.tsx
index 5bee91a9b..b1bc52c14 100644
--- a/apps/web/src/app/(signing)/sign/[token]/date-field.tsx
+++ b/apps/web/src/app/(signing)/sign/[token]/date-field.tsx
@@ -139,11 +139,15 @@ export const DateField = ({
       )}
 
       {!field.inserted && (
-        <p className="group-hover:text-primary text-muted-foreground text-lg duration-200">Date</p>
+        <p className="group-hover:text-primary text-muted-foreground duration-200 group-hover:text-yellow-300">
+          Date
+        </p>
       )}
 
       {field.inserted && (
-        <p className="text-muted-foreground text-sm duration-200">{localDateString}</p>
+        <p className="text-muted-foreground dark:text-background/80 text-sm duration-200">
+          {localDateString}
+        </p>
       )}
     </SigningFieldContainer>
   );
diff --git a/apps/web/src/app/(signing)/sign/[token]/dropdown-field.tsx b/apps/web/src/app/(signing)/sign/[token]/dropdown-field.tsx
new file mode 100644
index 000000000..c50e616ee
--- /dev/null
+++ b/apps/web/src/app/(signing)/sign/[token]/dropdown-field.tsx
@@ -0,0 +1,209 @@
+'use client';
+
+import { useEffect, useState, useTransition } from 'react';
+
+import { useRouter } from 'next/navigation';
+
+import { Loader } from 'lucide-react';
+
+import { DO_NOT_INVALIDATE_QUERY_ON_MUTATION } from '@documenso/lib/constants/trpc';
+import { AppError, AppErrorCode } from '@documenso/lib/errors/app-error';
+import type { TRecipientActionAuth } from '@documenso/lib/types/document-auth';
+import { ZDropdownFieldMeta } from '@documenso/lib/types/field-meta';
+import type { Recipient } from '@documenso/prisma/client';
+import type { FieldWithSignatureAndFieldMeta } from '@documenso/prisma/types/field-with-signature-and-fieldmeta';
+import { trpc } from '@documenso/trpc/react';
+import type {
+  TRemovedSignedFieldWithTokenMutationSchema,
+  TSignFieldWithTokenMutationSchema,
+} from '@documenso/trpc/server/field-router/schema';
+import { cn } from '@documenso/ui/lib/utils';
+import {
+  Select,
+  SelectContent,
+  SelectItem,
+  SelectTrigger,
+  SelectValue,
+} from '@documenso/ui/primitives/select';
+import { useToast } from '@documenso/ui/primitives/use-toast';
+
+import { useRequiredDocumentAuthContext } from './document-auth-provider';
+import { SigningFieldContainer } from './signing-field-container';
+
+export type DropdownFieldProps = {
+  field: FieldWithSignatureAndFieldMeta;
+  recipient: Recipient;
+  onSignField?: (value: TSignFieldWithTokenMutationSchema) => Promise<void> | void;
+  onUnsignField?: (value: TRemovedSignedFieldWithTokenMutationSchema) => Promise<void> | void;
+};
+
+export const DropdownField = ({
+  field,
+  recipient,
+  onSignField,
+  onUnsignField,
+}: DropdownFieldProps) => {
+  const router = useRouter();
+  const { toast } = useToast();
+  const [isPending, startTransition] = useTransition();
+
+  const { executeActionAuthProcedure } = useRequiredDocumentAuthContext();
+
+  const parsedFieldMeta = ZDropdownFieldMeta.parse(field.fieldMeta);
+  const isReadOnly = parsedFieldMeta?.readOnly;
+  const defaultValue = parsedFieldMeta?.defaultValue;
+  const [localChoice, setLocalChoice] = useState(parsedFieldMeta.defaultValue ?? '');
+
+  const { mutateAsync: signFieldWithToken, isLoading: isSignFieldWithTokenLoading } =
+    trpc.field.signFieldWithToken.useMutation(DO_NOT_INVALIDATE_QUERY_ON_MUTATION);
+
+  const {
+    mutateAsync: removeSignedFieldWithToken,
+    isLoading: isRemoveSignedFieldWithTokenLoading,
+  } = trpc.field.removeSignedFieldWithToken.useMutation(DO_NOT_INVALIDATE_QUERY_ON_MUTATION);
+
+  const isLoading = isSignFieldWithTokenLoading || isRemoveSignedFieldWithTokenLoading || isPending;
+  const shouldAutoSignField =
+    (!field.inserted && localChoice) || (!field.inserted && isReadOnly && defaultValue);
+
+  const onSign = async (authOptions?: TRecipientActionAuth) => {
+    try {
+      if (!localChoice) {
+        return;
+      }
+
+      const payload: TSignFieldWithTokenMutationSchema = {
+        token: recipient.token,
+        fieldId: field.id,
+        value: localChoice,
+        isBase64: true,
+        authOptions,
+      };
+
+      if (onSignField) {
+        await onSignField(payload);
+      } else {
+        await signFieldWithToken(payload);
+      }
+
+      setLocalChoice('');
+      startTransition(() => router.refresh());
+    } catch (err) {
+      const error = AppError.parseError(err);
+
+      if (error.code === AppErrorCode.UNAUTHORIZED) {
+        throw error;
+      }
+
+      console.error(err);
+
+      toast({
+        title: 'Error',
+        description: 'An error occurred while signing the document.',
+        variant: 'destructive',
+      });
+    }
+  };
+
+  const onPreSign = () => {
+    return true;
+  };
+
+  const onRemove = async () => {
+    try {
+      const payload: TRemovedSignedFieldWithTokenMutationSchema = {
+        token: recipient.token,
+        fieldId: field.id,
+      };
+
+      if (onUnsignField) {
+        await onUnsignField(payload);
+        return;
+      } else {
+        await removeSignedFieldWithToken(payload);
+      }
+
+      setLocalChoice(parsedFieldMeta.defaultValue ?? '');
+      startTransition(() => router.refresh());
+    } catch (err) {
+      console.error(err);
+
+      toast({
+        title: 'Error',
+        description: 'An error occurred while removing the signature.',
+        variant: 'destructive',
+      });
+    }
+  };
+
+  const handleSelectItem = (val: string) => {
+    setLocalChoice(val);
+  };
+
+  useEffect(() => {
+    if (!field.inserted && localChoice) {
+      void executeActionAuthProcedure({
+        onReauthFormSubmit: async (authOptions) => await onSign(authOptions),
+        actionTarget: field.type,
+      });
+    }
+  }, [localChoice]);
+
+  useEffect(() => {
+    if (shouldAutoSignField) {
+      void executeActionAuthProcedure({
+        onReauthFormSubmit: async (authOptions) => await onSign(authOptions),
+        actionTarget: field.type,
+      });
+    }
+  }, []);
+
+  return (
+    <div className="pointer-events-none">
+      <SigningFieldContainer
+        field={field}
+        onPreSign={onPreSign}
+        onSign={onSign}
+        onRemove={onRemove}
+        type="Dropdown"
+      >
+        {isLoading && (
+          <div className="bg-background absolute inset-0 flex items-center justify-center rounded-md">
+            <Loader className="text-primary h-5 w-5 animate-spin md:h-8 md:w-8" />
+          </div>
+        )}
+
+        {!field.inserted && (
+          <p className="group-hover:text-primary text-muted-foreground flex flex-col items-center justify-center duration-200">
+            <Select value={parsedFieldMeta.defaultValue} onValueChange={handleSelectItem}>
+              <SelectTrigger
+                className={cn(
+                  'text-muted-foreground z-10 h-full w-full border-none ring-0 focus:ring-0',
+                  {
+                    'hover:text-red-300': parsedFieldMeta.required,
+                    'hover:text-yellow-300': !parsedFieldMeta.required,
+                  },
+                )}
+              >
+                <SelectValue placeholder={'-- Select --'} />
+              </SelectTrigger>
+              <SelectContent className="w-full ring-0 focus:ring-0" position="popper">
+                {parsedFieldMeta?.values?.map((item, index) => (
+                  <SelectItem key={index} value={item.value} className="ring-0 focus:ring-0">
+                    {item.value}
+                  </SelectItem>
+                ))}
+              </SelectContent>
+            </Select>
+          </p>
+        )}
+
+        {field.inserted && (
+          <p className="text-muted-foreground dark:text-background/80 flex items-center justify-center gap-x-1 duration-200">
+            {field.customText}
+          </p>
+        )}
+      </SigningFieldContainer>
+    </div>
+  );
+};
diff --git a/apps/web/src/app/(signing)/sign/[token]/email-field.tsx b/apps/web/src/app/(signing)/sign/[token]/email-field.tsx
index 7be54f76b..9ff79e399 100644
--- a/apps/web/src/app/(signing)/sign/[token]/email-field.tsx
+++ b/apps/web/src/app/(signing)/sign/[token]/email-field.tsx
@@ -119,10 +119,16 @@ export const EmailField = ({ field, recipient, onSignField, onUnsignField }: Ema
       )}
 
       {!field.inserted && (
-        <p className="group-hover:text-primary text-muted-foreground text-lg duration-200">Email</p>
+        <p className="group-hover:text-primary text-muted-foreground duration-200 group-hover:text-yellow-300">
+          Email
+        </p>
       )}
 
-      {field.inserted && <p className="text-muted-foreground duration-200">{field.customText}</p>}
+      {field.inserted && (
+        <p className="text-muted-foreground dark:text-background/80 truncate duration-200">
+          {field.customText}
+        </p>
+      )}
     </SigningFieldContainer>
   );
 };
diff --git a/apps/web/src/app/(signing)/sign/[token]/name-field.tsx b/apps/web/src/app/(signing)/sign/[token]/name-field.tsx
index 1b52d77d5..f9c1f8edc 100644
--- a/apps/web/src/app/(signing)/sign/[token]/name-field.tsx
+++ b/apps/web/src/app/(signing)/sign/[token]/name-field.tsx
@@ -163,10 +163,16 @@ export const NameField = ({ field, recipient, onSignField, onUnsignField }: Name
       )}
 
       {!field.inserted && (
-        <p className="group-hover:text-primary text-muted-foreground text-lg duration-200">Name</p>
+        <p className="group-hover:text-primary text-muted-foreground duration-200 group-hover:text-yellow-300">
+          Name
+        </p>
       )}
 
-      {field.inserted && <p className="text-muted-foreground duration-200">{field.customText}</p>}
+      {field.inserted && (
+        <p className="text-muted-foreground dark:text-background/80 truncate duration-200">
+          {field.customText}
+        </p>
+      )}
 
       <Dialog open={showFullNameModal} onOpenChange={setShowFullNameModal}>
         <DialogContent>
diff --git a/apps/web/src/app/(signing)/sign/[token]/number-field.tsx b/apps/web/src/app/(signing)/sign/[token]/number-field.tsx
new file mode 100644
index 000000000..79a91d6b5
--- /dev/null
+++ b/apps/web/src/app/(signing)/sign/[token]/number-field.tsx
@@ -0,0 +1,337 @@
+'use client';
+
+import { useEffect, useState, useTransition } from 'react';
+
+import { useRouter } from 'next/navigation';
+
+import { Hash, Loader } from 'lucide-react';
+
+import { validateNumberField } from '@documenso/lib/advanced-fields-validation/validate-number';
+import { DO_NOT_INVALIDATE_QUERY_ON_MUTATION } from '@documenso/lib/constants/trpc';
+import { AppError, AppErrorCode } from '@documenso/lib/errors/app-error';
+import type { TRecipientActionAuth } from '@documenso/lib/types/document-auth';
+import { ZNumberFieldMeta } from '@documenso/lib/types/field-meta';
+import type { Recipient } from '@documenso/prisma/client';
+import type { FieldWithSignature } from '@documenso/prisma/types/field-with-signature';
+import { trpc } from '@documenso/trpc/react';
+import type {
+  TRemovedSignedFieldWithTokenMutationSchema,
+  TSignFieldWithTokenMutationSchema,
+} from '@documenso/trpc/server/field-router/schema';
+import { cn } from '@documenso/ui/lib/utils';
+import { Button } from '@documenso/ui/primitives/button';
+import { Dialog, DialogContent, DialogFooter, DialogTitle } from '@documenso/ui/primitives/dialog';
+import { Input } from '@documenso/ui/primitives/input';
+import { useToast } from '@documenso/ui/primitives/use-toast';
+
+import { useRequiredDocumentAuthContext } from './document-auth-provider';
+import { SigningFieldContainer } from './signing-field-container';
+
+type ValidationErrors = {
+  isNumber: string[];
+  required: string[];
+  minValue: string[];
+  maxValue: string[];
+  numberFormat: string[];
+};
+
+export type NumberFieldProps = {
+  field: FieldWithSignature;
+  recipient: Recipient;
+  onSignField?: (value: TSignFieldWithTokenMutationSchema) => Promise<void> | void;
+  onUnsignField?: (value: TRemovedSignedFieldWithTokenMutationSchema) => Promise<void> | void;
+};
+
+export const NumberField = ({ field, recipient, onSignField, onUnsignField }: NumberFieldProps) => {
+  const router = useRouter();
+  const { toast } = useToast();
+  const [isPending, startTransition] = useTransition();
+  const [showRadioModal, setShowRadioModal] = useState(false);
+
+  const parsedFieldMeta = field.fieldMeta ? ZNumberFieldMeta.parse(field.fieldMeta) : null;
+  const isReadOnly = parsedFieldMeta?.readOnly;
+  const defaultValue = parsedFieldMeta?.value;
+  const [localNumber, setLocalNumber] = useState(
+    parsedFieldMeta?.value ? String(parsedFieldMeta.value) : '0',
+  );
+
+  const initialErrors: ValidationErrors = {
+    isNumber: [],
+    required: [],
+    minValue: [],
+    maxValue: [],
+    numberFormat: [],
+  };
+
+  const [errors, setErrors] = useState(initialErrors);
+
+  const { executeActionAuthProcedure } = useRequiredDocumentAuthContext();
+
+  const { mutateAsync: signFieldWithToken, isLoading: isSignFieldWithTokenLoading } =
+    trpc.field.signFieldWithToken.useMutation(DO_NOT_INVALIDATE_QUERY_ON_MUTATION);
+
+  const {
+    mutateAsync: removeSignedFieldWithToken,
+    isLoading: isRemoveSignedFieldWithTokenLoading,
+  } = trpc.field.removeSignedFieldWithToken.useMutation(DO_NOT_INVALIDATE_QUERY_ON_MUTATION);
+
+  const isLoading = isSignFieldWithTokenLoading || isRemoveSignedFieldWithTokenLoading || isPending;
+
+  const handleNumberChange = (e: React.ChangeEvent<HTMLInputElement>) => {
+    const text = e.target.value;
+    setLocalNumber(text);
+
+    if (parsedFieldMeta) {
+      const validationErrors = validateNumberField(text, parsedFieldMeta, true);
+      setErrors({
+        isNumber: validationErrors.filter((error) => error.includes('valid number')),
+        required: validationErrors.filter((error) => error.includes('required')),
+        minValue: validationErrors.filter((error) => error.includes('minimum value')),
+        maxValue: validationErrors.filter((error) => error.includes('maximum value')),
+        numberFormat: validationErrors.filter((error) => error.includes('number format')),
+      });
+    } else {
+      const validationErrors = validateNumberField(text);
+      setErrors((prevErrors) => ({
+        ...prevErrors,
+        isNumber: validationErrors.filter((error) => error.includes('valid number')),
+      }));
+    }
+  };
+
+  const onDialogSignClick = () => {
+    setShowRadioModal(false);
+
+    void executeActionAuthProcedure({
+      onReauthFormSubmit: async (authOptions) => await onSign(authOptions),
+      actionTarget: field.type,
+    });
+  };
+
+  const onSign = async (authOptions?: TRecipientActionAuth) => {
+    try {
+      if (!localNumber || Object.values(errors).some((error) => error.length > 0)) {
+        return;
+      }
+
+      const payload: TSignFieldWithTokenMutationSchema = {
+        token: recipient.token,
+        fieldId: field.id,
+        value: localNumber,
+        isBase64: true,
+        authOptions,
+      };
+
+      if (onSignField) {
+        await onSignField(payload);
+        return;
+      }
+
+      await signFieldWithToken(payload);
+
+      setLocalNumber('');
+
+      startTransition(() => router.refresh());
+    } catch (err) {
+      const error = AppError.parseError(err);
+
+      if (error.code === AppErrorCode.UNAUTHORIZED) {
+        throw error;
+      }
+
+      console.error(err);
+
+      toast({
+        title: 'Error',
+        description: 'An error occurred while signing the document.',
+        variant: 'destructive',
+      });
+    }
+  };
+
+  const onPreSign = () => {
+    setShowRadioModal(true);
+
+    if (localNumber && parsedFieldMeta) {
+      const validationErrors = validateNumberField(localNumber, parsedFieldMeta, true);
+      setErrors({
+        isNumber: validationErrors.filter((error) => error.includes('valid number')),
+        required: validationErrors.filter((error) => error.includes('required')),
+        minValue: validationErrors.filter((error) => error.includes('minimum value')),
+        maxValue: validationErrors.filter((error) => error.includes('maximum value')),
+        numberFormat: validationErrors.filter((error) => error.includes('number format')),
+      });
+    }
+
+    return false;
+  };
+
+  const onRemove = async () => {
+    try {
+      const payload: TRemovedSignedFieldWithTokenMutationSchema = {
+        token: recipient.token,
+        fieldId: field.id,
+      };
+
+      if (onUnsignField) {
+        await onUnsignField(payload);
+        return;
+      }
+
+      await removeSignedFieldWithToken(payload);
+
+      setLocalNumber(parsedFieldMeta?.value ? String(parsedFieldMeta?.value) : '');
+
+      startTransition(() => router.refresh());
+    } catch (err) {
+      console.error(err);
+
+      toast({
+        title: 'Error',
+        description: 'An error occurred while removing the signature.',
+        variant: 'destructive',
+      });
+    }
+  };
+
+  useEffect(() => {
+    if (!showRadioModal) {
+      setLocalNumber(parsedFieldMeta?.value ? String(parsedFieldMeta.value) : '0');
+      setErrors(initialErrors);
+    }
+  }, [showRadioModal]);
+
+  useEffect(() => {
+    if (
+      (!field.inserted && defaultValue && localNumber) ||
+      (!field.inserted && isReadOnly && defaultValue)
+    ) {
+      void executeActionAuthProcedure({
+        onReauthFormSubmit: async (authOptions) => await onSign(authOptions),
+        actionTarget: field.type,
+      });
+    }
+  }, []);
+
+  let fieldDisplayName = 'Number';
+
+  if (parsedFieldMeta?.label) {
+    fieldDisplayName = parsedFieldMeta.label.length > 10 ? parsedFieldMeta.label.substring(0, 10) + '...' : parsedFieldMeta.label;
+  }
+
+  const userInputHasErrors = Object.values(errors).some((error) => error.length > 0);
+
+  return (
+    <SigningFieldContainer
+      field={field}
+      onPreSign={onPreSign}
+      onSign={onSign}
+      onRemove={onRemove}
+      type="Signature"
+    >
+      {isLoading && (
+        <div className="bg-background absolute inset-0 flex items-center justify-center rounded-md">
+          <Loader className="text-primary h-5 w-5 animate-spin md:h-8 md:w-8" />
+        </div>
+      )}
+
+      {!field.inserted && (
+        <p
+          className={cn(
+            'group-hover:text-primary text-muted-foreground flex flex-col items-center justify-center duration-200',
+            {
+              'group-hover:text-yellow-300': !field.inserted && !parsedFieldMeta?.required,
+              'group-hover:text-red-300': !field.inserted && parsedFieldMeta?.required,
+            },
+          )}
+        >
+          <span className="flex items-center justify-center gap-x-1 text-sm">
+            <Hash className='h-4 w-4' /> {fieldDisplayName}
+          </span>
+        </p>
+      )}
+
+      {field.inserted && (
+        <p className="text-muted-foreground dark:text-background/80 flex items-center justify-center gap-x-1 duration-200">
+          {field.customText}
+        </p>
+      )}
+
+      <Dialog open={showRadioModal} onOpenChange={setShowRadioModal}>
+        <DialogContent>
+          <DialogTitle>
+            {parsedFieldMeta?.label ? parsedFieldMeta?.label : 'Add number'}
+          </DialogTitle>
+
+          <div>
+            <Input
+              type="text"
+              placeholder={parsedFieldMeta?.placeholder ?? ''}
+              className={cn('mt-2 w-full rounded-md', {
+                'border-2 border-red-300 ring-2 ring-red-200 ring-offset-2 ring-offset-red-200 focus-visible:border-red-400 focus-visible:ring-4 focus-visible:ring-red-200 focus-visible:ring-offset-2 focus-visible:ring-offset-red-200':
+                  userInputHasErrors,
+              })}
+              value={localNumber}
+              onChange={handleNumberChange}
+            />
+          </div>
+
+          {userInputHasErrors && (
+            <div>
+              {errors.isNumber?.map((error, index) => (
+                <p key={index} className="mt-2 text-sm text-red-500">
+                  {error}
+                </p>
+              ))}
+              {errors.required?.map((error, index) => (
+                <p key={index} className="mt-2 text-sm text-red-500">
+                  {error}
+                </p>
+              ))}
+              {errors.minValue?.map((error, index) => (
+                <p key={index} className="mt-2 text-sm text-red-500">
+                  {error}
+                </p>
+              ))}
+              {errors.maxValue?.map((error, index) => (
+                <p key={index} className="mt-2 text-sm text-red-500">
+                  {error}
+                </p>
+              ))}
+              {errors.numberFormat?.map((error, index) => (
+                <p key={index} className="mt-2 text-sm text-red-500">
+                  {error}
+                </p>
+              ))}
+            </div>
+          )}
+
+          <DialogFooter>
+            <div className="flex w-full flex-1 flex-nowrap gap-4">
+              <Button
+                type="button"
+                className="dark:bg-muted dark:hover:bg-muted/80 flex-1  bg-black/5 hover:bg-black/10"
+                variant="secondary"
+                onClick={() => {
+                  setShowRadioModal(false);
+                  setLocalNumber('');
+                }}
+              >
+                Cancel
+              </Button>
+
+              <Button
+                type="button"
+                className="flex-1"
+                disabled={!localNumber || userInputHasErrors}
+                onClick={() => onDialogSignClick()}
+              >
+                Save
+              </Button>
+            </div>
+          </DialogFooter>
+        </DialogContent>
+      </Dialog>
+    </SigningFieldContainer>
+  );
+};
diff --git a/apps/web/src/app/(signing)/sign/[token]/radio-field.tsx b/apps/web/src/app/(signing)/sign/[token]/radio-field.tsx
new file mode 100644
index 000000000..d09205ca0
--- /dev/null
+++ b/apps/web/src/app/(signing)/sign/[token]/radio-field.tsx
@@ -0,0 +1,190 @@
+'use client';
+
+import { useEffect, useState, useTransition } from 'react';
+
+import { useRouter } from 'next/navigation';
+
+import { Loader } from 'lucide-react';
+
+import { DO_NOT_INVALIDATE_QUERY_ON_MUTATION } from '@documenso/lib/constants/trpc';
+import { AppError, AppErrorCode } from '@documenso/lib/errors/app-error';
+import type { TRecipientActionAuth } from '@documenso/lib/types/document-auth';
+import { ZRadioFieldMeta } from '@documenso/lib/types/field-meta';
+import type { Recipient } from '@documenso/prisma/client';
+import type { FieldWithSignatureAndFieldMeta } from '@documenso/prisma/types/field-with-signature-and-fieldmeta';
+import { trpc } from '@documenso/trpc/react';
+import type {
+  TRemovedSignedFieldWithTokenMutationSchema,
+  TSignFieldWithTokenMutationSchema,
+} from '@documenso/trpc/server/field-router/schema';
+import { Label } from '@documenso/ui/primitives/label';
+import { RadioGroup, RadioGroupItem } from '@documenso/ui/primitives/radio-group';
+import { useToast } from '@documenso/ui/primitives/use-toast';
+
+import { useRequiredDocumentAuthContext } from './document-auth-provider';
+import { SigningFieldContainer } from './signing-field-container';
+
+export type RadioFieldProps = {
+  field: FieldWithSignatureAndFieldMeta;
+  recipient: Recipient;
+  onSignField?: (value: TSignFieldWithTokenMutationSchema) => Promise<void> | void;
+  onUnsignField?: (value: TRemovedSignedFieldWithTokenMutationSchema) => Promise<void> | void;
+};
+
+export const RadioField = ({ field, recipient, onSignField, onUnsignField }: RadioFieldProps) => {
+  const router = useRouter();
+  const { toast } = useToast();
+  const [isPending, startTransition] = useTransition();
+
+  const parsedFieldMeta = ZRadioFieldMeta.parse(field.fieldMeta);
+  const values = parsedFieldMeta.values?.map((item) => ({
+    ...item,
+    value: item.value.length > 0 ? item.value : `empty-value-${item.id}`,
+  }));
+  const checkedItem = values?.find((item) => item.checked);
+  const defaultValue = !field.inserted && !!checkedItem ? checkedItem.value : '';
+
+  const [selectedOption, setSelectedOption] = useState(defaultValue);
+
+  const { executeActionAuthProcedure } = useRequiredDocumentAuthContext();
+
+  const { mutateAsync: signFieldWithToken, isLoading: isSignFieldWithTokenLoading } =
+    trpc.field.signFieldWithToken.useMutation(DO_NOT_INVALIDATE_QUERY_ON_MUTATION);
+
+  const {
+    mutateAsync: removeSignedFieldWithToken,
+    isLoading: isRemoveSignedFieldWithTokenLoading,
+  } = trpc.field.removeSignedFieldWithToken.useMutation(DO_NOT_INVALIDATE_QUERY_ON_MUTATION);
+
+  const isLoading = isSignFieldWithTokenLoading || isRemoveSignedFieldWithTokenLoading || isPending;
+  const shouldAutoSignField =
+    (!field.inserted && selectedOption) ||
+    (!field.inserted && defaultValue) ||
+    (!field.inserted && parsedFieldMeta.readOnly && defaultValue);
+
+  const onSign = async (authOptions?: TRecipientActionAuth) => {
+    try {
+      if (!selectedOption) {
+        return;
+      }
+
+      const payload: TSignFieldWithTokenMutationSchema = {
+        token: recipient.token,
+        fieldId: field.id,
+        value: selectedOption,
+        isBase64: true,
+        authOptions,
+      };
+
+      if (onSignField) {
+        await onSignField(payload);
+      } else {
+        await signFieldWithToken(payload);
+      }
+
+      setSelectedOption('');
+      startTransition(() => router.refresh());
+    } catch (err) {
+      const error = AppError.parseError(err);
+
+      if (error.code === AppErrorCode.UNAUTHORIZED) {
+        throw error;
+      }
+
+      console.error(err);
+
+      toast({
+        title: 'Error',
+        description: 'An error occurred while signing the document.',
+        variant: 'destructive',
+      });
+    }
+  };
+
+  const onRemove = async () => {
+    try {
+      const payload: TRemovedSignedFieldWithTokenMutationSchema = {
+        token: recipient.token,
+        fieldId: field.id,
+      };
+
+      if (onUnsignField) {
+        await onUnsignField(payload);
+      } else {
+        await removeSignedFieldWithToken(payload);
+      }
+
+      setSelectedOption('');
+
+      startTransition(() => router.refresh());
+    } catch (err) {
+      console.error(err);
+
+      toast({
+        title: 'Error',
+        description: 'An error occurred while removing the signature.',
+        variant: 'destructive',
+      });
+    }
+  };
+
+  const handleSelectItem = (selectedOption: string) => {
+    setSelectedOption(selectedOption);
+  };
+
+  useEffect(() => {
+    if (shouldAutoSignField) {
+      void executeActionAuthProcedure({
+        onReauthFormSubmit: async (authOptions) => await onSign(authOptions),
+        actionTarget: field.type,
+      });
+    }
+  }, [selectedOption, field]);
+
+  return (
+    <SigningFieldContainer field={field} onSign={onSign} onRemove={onRemove} type="Radio">
+      {isLoading && (
+        <div className="bg-background absolute inset-0 z-20 flex items-center justify-center rounded-md">
+          <Loader className="text-primary h-5 w-5 animate-spin md:h-8 md:w-8" />
+        </div>
+      )}
+
+      {!field.inserted && (
+        <RadioGroup onValueChange={(value) => handleSelectItem(value)} className="z-10">
+          {values?.map((item, index) => (
+            <div key={index} className="flex items-center gap-x-1.5">
+              <RadioGroupItem
+                className="h-4 w-4 shrink-0"
+                value={item.value}
+                id={`option-${index}`}
+                checked={item.checked}
+              />
+
+              <Label htmlFor={`option-${index}`}>
+                {item.value.includes('empty-value-') ? '' : item.value}
+              </Label>
+            </div>
+          ))}
+        </RadioGroup>
+      )}
+
+      {field.inserted && (
+        <RadioGroup>
+          {values?.map((item, index) => (
+            <div key={index} className="flex items-center gap-x-1.5">
+                <RadioGroupItem
+                  className=""
+                  value={item.value}
+                  id={`option-${index}`}
+                  checked={item.value === field.customText}
+                />
+                <Label htmlFor={`option-${index}`}>
+                  {item.value.includes('empty-value-') ? '' : item.value}
+                </Label>
+            </div>
+          ))}
+        </RadioGroup>
+      )}
+    </SigningFieldContainer>
+  );
+};
diff --git a/apps/web/src/app/(signing)/sign/[token]/signature-field.tsx b/apps/web/src/app/(signing)/sign/[token]/signature-field.tsx
index e6c39ab08..348f1abf3 100644
--- a/apps/web/src/app/(signing)/sign/[token]/signature-field.tsx
+++ b/apps/web/src/app/(signing)/sign/[token]/signature-field.tsx
@@ -190,7 +190,7 @@ export const SignatureField = ({
       )}
 
       {state === 'empty' && (
-        <p className="group-hover:text-primary font-signature text-muted-foreground text-lg duration-200 sm:text-xl md:text-2xl lg:text-3xl">
+        <p className="group-hover:text-primary font-signature text-muted-foreground duration-200 group-hover:text-yellow-300 text-xl">
           Signature
         </p>
       )}
@@ -199,12 +199,12 @@ export const SignatureField = ({
         <img
           src={signature.signatureImageAsBase64}
           alt={`Signature for ${recipient.name}`}
-          className="h-full w-full object-contain dark:invert"
+          className="h-full w-full object-contain"
         />
       )}
 
       {state === 'signed-text' && (
-        <p className="font-signature text-muted-foreground text-lg duration-200 sm:text-xl md:text-2xl lg:text-3xl">
+        <p className="font-signature text-muted-foreground dark:text-background text-lg duration-200 sm:text-xl md:text-2xl lg:text-3xl">
           {/* This optional chaining is intentional, we don't want to move the check into the condition above */}
           {signature?.typedSignature}
         </p>
diff --git a/apps/web/src/app/(signing)/sign/[token]/signing-field-container.tsx b/apps/web/src/app/(signing)/sign/[token]/signing-field-container.tsx
index 825a15d0f..c73e35306 100644
--- a/apps/web/src/app/(signing)/sign/[token]/signing-field-container.tsx
+++ b/apps/web/src/app/(signing)/sign/[token]/signing-field-container.tsx
@@ -2,10 +2,14 @@
 
 import React from 'react';
 
+import { X } from 'lucide-react';
+
 import { type TRecipientActionAuth } from '@documenso/lib/types/document-auth';
+import { ZFieldMetaSchema } from '@documenso/lib/types/field-meta';
 import { FieldType } from '@documenso/prisma/client';
 import type { FieldWithSignature } from '@documenso/prisma/types/field-with-signature';
 import { FieldRootContainer } from '@documenso/ui/components/field/field';
+import { cn } from '@documenso/ui/lib/utils';
 import { Tooltip, TooltipContent, TooltipTrigger } from '@documenso/ui/primitives/tooltip';
 
 import { useRequiredDocumentAuthContext } from './document-auth-provider';
@@ -34,8 +38,8 @@ export type SignatureFieldProps = {
    * The auth values will be passed in if available.
    */
   onSign?: (documentAuthValue?: TRecipientActionAuth) => Promise<void> | void;
-  onRemove?: () => Promise<void> | void;
-  type?: 'Date' | 'Email' | 'Name' | 'Signature';
+  onRemove?: (fieldType?: string) => Promise<void> | void;
+  type?: 'Date' | 'Email' | 'Name' | 'Signature' | 'Radio' | 'Dropdown' | 'Number' | 'Checkbox';
   tooltipText?: string | null;
 };
 
@@ -51,6 +55,9 @@ export const SigningFieldContainer = ({
 }: SignatureFieldProps) => {
   const { executeActionAuthProcedure, isAuthRedirectRequired } = useRequiredDocumentAuthContext();
 
+  const parsedFieldMeta = field.fieldMeta ? ZFieldMetaSchema.parse(field.fieldMeta) : undefined;
+  const readOnlyField = parsedFieldMeta?.readOnly || false;
+
   const handleInsertField = async () => {
     if (field.inserted || !onSign) {
       return;
@@ -102,41 +109,70 @@ export const SigningFieldContainer = ({
     await onRemove?.();
   };
 
+  const onClearCheckBoxValues = async (fieldType?: string) => {
+    if (!field.inserted) {
+      return;
+    }
+
+    await onRemove?.(fieldType);
+  };
+
   return (
-    <FieldRootContainer field={field}>
-      {!field.inserted && !loading && (
-        <button
-          type="submit"
-          className="absolute inset-0 z-10 h-full w-full"
-          onClick={async () => handleInsertField()}
-        />
-      )}
+    <div className={cn(type === 'Checkbox' ? 'group' : '')}>
+      <FieldRootContainer field={field}>
+        {!field.inserted && !loading && !readOnlyField && (
+          <button
+            type="submit"
+            className="absolute inset-0 z-10 h-full w-full rounded-md border"
+            onClick={async () => handleInsertField()}
+          />
+        )}
 
-      {type === 'Date' && field.inserted && !loading && (
-        <Tooltip delayDuration={0}>
-          <TooltipTrigger asChild>
-            <button
-              className="text-destructive bg-background/40 absolute inset-0 z-10 flex h-full w-full items-center justify-center rounded-md text-sm opacity-0 backdrop-blur-sm duration-200 group-hover:opacity-100"
-              onClick={onRemoveSignedFieldClick}
-            >
-              Remove
-            </button>
-          </TooltipTrigger>
+        {readOnlyField && (
+          <button className="bg-background/40 absolute inset-0 z-10 flex h-full w-full items-center justify-center rounded-md text-sm opacity-0 duration-200 group-hover:opacity-100">
+            <span className="bg-foreground/50 dark:bg-background/50 text-background dark:text-foreground rounded-xl p-2">
+              Read only field
+            </span>
+          </button>
+        )}
 
-          {tooltipText && <TooltipContent className="max-w-xs">{tooltipText}</TooltipContent>}
-        </Tooltip>
-      )}
+        {type === 'Date' && field.inserted && !loading && !readOnlyField && (
+          <Tooltip delayDuration={0}>
+            <TooltipTrigger asChild>
+              <button
+                className="text-destructive bg-background/40 absolute inset-0 z-10 flex h-full w-full items-center justify-center rounded-md text-sm opacity-0 duration-200 group-hover:opacity-100"
+                onClick={onRemoveSignedFieldClick}
+              >
+                Remove
+              </button>
+            </TooltipTrigger>
 
-      {type !== 'Date' && field.inserted && !loading && (
-        <button
-          className="text-destructive bg-background/40 absolute inset-0 z-10 flex h-full w-full items-center justify-center rounded-md text-sm opacity-0 backdrop-blur-sm duration-200 group-hover:opacity-100"
-          onClick={onRemoveSignedFieldClick}
-        >
-          Remove
-        </button>
-      )}
+            {tooltipText && <TooltipContent className="max-w-xs">{tooltipText}</TooltipContent>}
+          </Tooltip>
+        )}
 
-      {children}
-    </FieldRootContainer>
+        {type === 'Checkbox' && field.inserted && !loading && !readOnlyField && (
+          <button
+            className="dark:bg-background absolute -bottom-10 flex items-center justify-evenly rounded-md border bg-gray-900 opacity-0 group-hover:opacity-100"
+            onClick={() => void onClearCheckBoxValues(type)}
+          >
+            <span className="dark:text-muted-foreground/50 dark:hover:text-muted-foreground dark:hover:bg-foreground/10 rounded-md p-1 text-gray-400 transition-colors hover:bg-white/10 hover:text-gray-100">
+              <X className="h-4 w-4" />
+            </span>
+          </button>
+        )}
+
+        {type !== 'Date' && type !== 'Checkbox' && field.inserted && !loading && !readOnlyField && (
+          <button
+            className="text-destructive bg-background/50 absolute inset-0 z-10 flex h-full w-full items-center justify-center rounded-md text-sm opacity-0 duration-200 group-hover:opacity-100"
+            onClick={onRemoveSignedFieldClick}
+          >
+            Remove
+          </button>
+        )}
+
+        {children}
+      </FieldRootContainer>
+    </div>
   );
 };
diff --git a/apps/web/src/app/(signing)/sign/[token]/signing-page-view.tsx b/apps/web/src/app/(signing)/sign/[token]/signing-page-view.tsx
index 4691d0d4c..11cf1d64a 100644
--- a/apps/web/src/app/(signing)/sign/[token]/signing-page-view.tsx
+++ b/apps/web/src/app/(signing)/sign/[token]/signing-page-view.tsx
@@ -4,9 +4,17 @@ import { DEFAULT_DOCUMENT_DATE_FORMAT } from '@documenso/lib/constants/date-form
 import { PDF_VIEWER_PAGE_SELECTOR } from '@documenso/lib/constants/pdf-viewer';
 import { DEFAULT_DOCUMENT_TIME_ZONE } from '@documenso/lib/constants/time-zones';
 import type { DocumentAndSender } from '@documenso/lib/server-only/document/get-document-by-token';
+import {
+  ZCheckboxFieldMeta,
+  ZDropdownFieldMeta,
+  ZNumberFieldMeta,
+  ZRadioFieldMeta,
+  ZTextFieldMeta,
+} from '@documenso/lib/types/field-meta';
 import type { CompletedField } from '@documenso/lib/types/fields';
 import type { Field, Recipient } from '@documenso/prisma/client';
 import { FieldType, RecipientRole } from '@documenso/prisma/client';
+import type { FieldWithSignatureAndFieldMeta } from '@documenso/prisma/types/field-with-signature-and-fieldmeta';
 import { Card, CardContent } from '@documenso/ui/primitives/card';
 import { ElementVisible } from '@documenso/ui/primitives/element-visible';
 import { LazyPDFViewer } from '@documenso/ui/primitives/lazy-pdf-viewer';
@@ -14,10 +22,14 @@ import { LazyPDFViewer } from '@documenso/ui/primitives/lazy-pdf-viewer';
 import { DocumentReadOnlyFields } from '~/components/document/document-read-only-fields';
 import { truncateTitle } from '~/helpers/truncate-title';
 
+import { CheckboxField } from './checkbox-field';
 import { DateField } from './date-field';
+import { DropdownField } from './dropdown-field';
 import { EmailField } from './email-field';
 import { SigningForm } from './form';
 import { NameField } from './name-field';
+import { NumberField } from './number-field';
+import { RadioField } from './radio-field';
 import { SignatureField } from './signature-field';
 import { TextField } from './text-field';
 
@@ -101,9 +113,41 @@ export const SigningPageView = ({
             .with(FieldType.EMAIL, () => (
               <EmailField key={field.id} field={field} recipient={recipient} />
             ))
-            .with(FieldType.TEXT, () => (
-              <TextField key={field.id} field={field} recipient={recipient} />
-            ))
+            .with(FieldType.TEXT, () => {
+              const fieldWithMeta: FieldWithSignatureAndFieldMeta = {
+                ...field,
+                fieldMeta: field.fieldMeta ? ZTextFieldMeta.parse(field.fieldMeta) : null,
+              };
+              return <TextField key={field.id} field={fieldWithMeta} recipient={recipient} />;
+            })
+            .with(FieldType.NUMBER, () => {
+              const fieldWithMeta: FieldWithSignatureAndFieldMeta = {
+                ...field,
+                fieldMeta: field.fieldMeta ? ZNumberFieldMeta.parse(field.fieldMeta) : null,
+              };
+              return <NumberField key={field.id} field={fieldWithMeta} recipient={recipient} />;
+            })
+            .with(FieldType.RADIO, () => {
+              const fieldWithMeta: FieldWithSignatureAndFieldMeta = {
+                ...field,
+                fieldMeta: field.fieldMeta ? ZRadioFieldMeta.parse(field.fieldMeta) : null,
+              };
+              return <RadioField key={field.id} field={fieldWithMeta} recipient={recipient} />;
+            })
+            .with(FieldType.CHECKBOX, () => {
+              const fieldWithMeta: FieldWithSignatureAndFieldMeta = {
+                ...field,
+                fieldMeta: field.fieldMeta ? ZCheckboxFieldMeta.parse(field.fieldMeta) : null,
+              };
+              return <CheckboxField key={field.id} field={fieldWithMeta} recipient={recipient} />;
+            })
+            .with(FieldType.DROPDOWN, () => {
+              const fieldWithMeta: FieldWithSignatureAndFieldMeta = {
+                ...field,
+                fieldMeta: field.fieldMeta ? ZDropdownFieldMeta.parse(field.fieldMeta) : null,
+              };
+              return <DropdownField key={field.id} field={fieldWithMeta} recipient={recipient} />;
+            })
             .otherwise(() => null),
         )}
       </ElementVisible>
diff --git a/apps/web/src/app/(signing)/sign/[token]/text-field.tsx b/apps/web/src/app/(signing)/sign/[token]/text-field.tsx
index ec063315d..6e2a7b405 100644
--- a/apps/web/src/app/(signing)/sign/[token]/text-field.tsx
+++ b/apps/web/src/app/(signing)/sign/[token]/text-field.tsx
@@ -4,29 +4,31 @@ import { useEffect, useState, useTransition } from 'react';
 
 import { useRouter } from 'next/navigation';
 
-import { Loader } from 'lucide-react';
+import { Loader, Type } from 'lucide-react';
 
+import { validateTextField } from '@documenso/lib/advanced-fields-validation/validate-text';
 import { DO_NOT_INVALIDATE_QUERY_ON_MUTATION } from '@documenso/lib/constants/trpc';
 import { AppError, AppErrorCode } from '@documenso/lib/errors/app-error';
 import type { TRecipientActionAuth } from '@documenso/lib/types/document-auth';
+import { ZTextFieldMeta } from '@documenso/lib/types/field-meta';
 import type { Recipient } from '@documenso/prisma/client';
-import type { FieldWithSignature } from '@documenso/prisma/types/field-with-signature';
+import type { FieldWithSignatureAndFieldMeta } from '@documenso/prisma/types/field-with-signature-and-fieldmeta';
 import { trpc } from '@documenso/trpc/react';
 import type {
   TRemovedSignedFieldWithTokenMutationSchema,
   TSignFieldWithTokenMutationSchema,
 } from '@documenso/trpc/server/field-router/schema';
+import { cn } from '@documenso/ui/lib/utils';
 import { Button } from '@documenso/ui/primitives/button';
 import { Dialog, DialogContent, DialogFooter, DialogTitle } from '@documenso/ui/primitives/dialog';
-import { Input } from '@documenso/ui/primitives/input';
-import { Label } from '@documenso/ui/primitives/label';
+import { Textarea } from '@documenso/ui/primitives/textarea';
 import { useToast } from '@documenso/ui/primitives/use-toast';
 
 import { useRequiredDocumentAuthContext } from './document-auth-provider';
 import { SigningFieldContainer } from './signing-field-container';
 
 export type TextFieldProps = {
-  field: FieldWithSignature;
+  field: FieldWithSignatureAndFieldMeta;
   recipient: Recipient;
   onSignField?: (value: TSignFieldWithTokenMutationSchema) => Promise<void> | void;
   onUnsignField?: (value: TRemovedSignedFieldWithTokenMutationSchema) => Promise<void> | void;
@@ -34,9 +36,16 @@ export type TextFieldProps = {
 
 export const TextField = ({ field, recipient, onSignField, onUnsignField }: TextFieldProps) => {
   const router = useRouter();
-
   const { toast } = useToast();
 
+  const initialErrors: Record<string, string[]> = {
+    required: [],
+    characterLimit: [],
+  };
+
+  const [errors, setErrors] = useState(initialErrors);
+  const userInputHasErrors = Object.values(errors).some((error) => error.length > 0);
+
   const { executeActionAuthProcedure } = useRequiredDocumentAuthContext();
 
   const [isPending, startTransition] = useTransition();
@@ -49,21 +58,52 @@ export const TextField = ({ field, recipient, onSignField, onUnsignField }: Text
     isLoading: isRemoveSignedFieldWithTokenLoading,
   } = trpc.field.removeSignedFieldWithToken.useMutation(DO_NOT_INVALIDATE_QUERY_ON_MUTATION);
 
+  const parsedFieldMeta = field.fieldMeta ? ZTextFieldMeta.parse(field.fieldMeta) : null;
+
   const isLoading = isSignFieldWithTokenLoading || isRemoveSignedFieldWithTokenLoading || isPending;
+  const shouldAutoSignField =
+    (!field.inserted && parsedFieldMeta?.text) ||
+    (!field.inserted && parsedFieldMeta?.text && parsedFieldMeta?.readOnly);
 
   const [showCustomTextModal, setShowCustomTextModal] = useState(false);
-  const [localText, setLocalCustomText] = useState('');
+  const [localText, setLocalCustomText] = useState(parsedFieldMeta?.text ?? '');
 
   useEffect(() => {
     if (!showCustomTextModal) {
-      setLocalCustomText('');
+      setLocalCustomText(parsedFieldMeta?.text ?? '');
+      setErrors(initialErrors);
     }
   }, [showCustomTextModal]);
 
+  const handleTextChange = (e: React.ChangeEvent<HTMLTextAreaElement>) => {
+    const text = e.target.value;
+    setLocalCustomText(text);
+
+    if (parsedFieldMeta) {
+      const validationErrors = validateTextField(text, parsedFieldMeta, true);
+      setErrors({
+        required: validationErrors.filter((error) => error.includes('required')),
+        characterLimit: validationErrors.filter((error) => error.includes('character limit')),
+      });
+    }
+  };
+
   /**
    * When the user clicks the sign button in the dialog where they enter the text field.
    */
   const onDialogSignClick = () => {
+    if (parsedFieldMeta) {
+      const validationErrors = validateTextField(localText, parsedFieldMeta, true);
+
+      if (validationErrors.length > 0) {
+        setErrors({
+          required: validationErrors.filter((error) => error.includes('required')),
+          characterLimit: validationErrors.filter((error) => error.includes('character limit')),
+        });
+        return;
+      }
+    }
+
     setShowCustomTextModal(false);
 
     void executeActionAuthProcedure({
@@ -73,17 +113,22 @@ export const TextField = ({ field, recipient, onSignField, onUnsignField }: Text
   };
 
   const onPreSign = () => {
-    if (!localText) {
-      setShowCustomTextModal(true);
-      return false;
+    setShowCustomTextModal(true);
+
+    if (localText && parsedFieldMeta) {
+      const validationErrors = validateTextField(localText, parsedFieldMeta, true);
+      setErrors({
+        required: validationErrors.filter((error) => error.includes('required')),
+        characterLimit: validationErrors.filter((error) => error.includes('character limit')),
+      });
     }
 
-    return true;
+    return false;
   };
 
   const onSign = async (authOptions?: TRecipientActionAuth) => {
     try {
-      if (!localText) {
+      if (!localText || userInputHasErrors) {
         return;
       }
 
@@ -136,6 +181,8 @@ export const TextField = ({ field, recipient, onSignField, onUnsignField }: Text
 
       await removeSignedFieldWithToken(payload);
 
+      setLocalCustomText(parsedFieldMeta?.text ?? '');
+
       startTransition(() => router.refresh());
     } catch (err) {
       console.error(err);
@@ -148,6 +195,34 @@ export const TextField = ({ field, recipient, onSignField, onUnsignField }: Text
     }
   };
 
+  useEffect(() => {
+    if (shouldAutoSignField) {
+      void executeActionAuthProcedure({
+        onReauthFormSubmit: async (authOptions) => await onSign(authOptions),
+        actionTarget: field.type,
+      });
+    }
+  }, []);
+
+  const parsedField = field.fieldMeta ? ZTextFieldMeta.parse(field.fieldMeta) : undefined;
+
+  const labelDisplay =
+    parsedField?.label && parsedField.label.length < 20
+      ? parsedField.label
+      : parsedField?.label
+      ? parsedField?.label.substring(0, 20) + '...'
+      : undefined;
+
+  const textDisplay =
+    parsedField?.text && parsedField.text.length < 20
+      ? parsedField.text
+      : parsedField?.text
+      ? parsedField?.text.substring(0, 20) + '...'
+      : undefined;
+
+  const fieldDisplayName = labelDisplay ? labelDisplay : textDisplay ? textDisplay : 'Add text';
+  const charactersRemaining = (parsedFieldMeta?.characterLimit ?? 0) - (localText.length ?? 0);
+
   return (
     <SigningFieldContainer
       field={field}
@@ -163,27 +238,69 @@ export const TextField = ({ field, recipient, onSignField, onUnsignField }: Text
       )}
 
       {!field.inserted && (
-        <p className="group-hover:text-primary text-muted-foreground text-lg duration-200">Text</p>
+        <p
+          className={cn(
+            'group-hover:text-primary text-muted-foreground flex flex-col items-center justify-center duration-200',
+            {
+              'group-hover:text-yellow-300': !field.inserted && !parsedFieldMeta?.required,
+              'group-hover:text-red-300': !field.inserted && parsedFieldMeta?.required,
+            },
+          )}
+        >
+          <span className="flex items-center justify-center gap-x-1">
+            <Type />
+            {fieldDisplayName}
+          </span>
+        </p>
       )}
 
-      {field.inserted && <p className="text-muted-foreground duration-200">{field.customText}</p>}
+      {field.inserted && (
+        <p className="text-muted-foreground dark:text-background/80 flex items-center justify-center gap-x-1 duration-200">
+          {field.customText.length < 20
+            ? field.customText
+            : field.customText.substring(0, 15) + '...'}
+        </p>
+      )}
 
       <Dialog open={showCustomTextModal} onOpenChange={setShowCustomTextModal}>
         <DialogContent>
-          <DialogTitle>
-            Enter your Text <span className="text-muted-foreground">({recipient.email})</span>
-          </DialogTitle>
+          <DialogTitle>{parsedFieldMeta?.label ? parsedFieldMeta?.label : 'Add Text'}</DialogTitle>
 
-          <div className="">
-            <Label htmlFor="custom-text">Custom Text</Label>
-
-            <Input
+          <div>
+            <Textarea
               id="custom-text"
-              className="border-border mt-2 w-full rounded-md border"
-              onChange={(e) => setLocalCustomText(e.target.value)}
+              placeholder={parsedFieldMeta?.placeholder ?? 'Enter your text here'}
+              className={cn('mt-2 w-full rounded-md', {
+                'border-2 border-red-300 ring-2 ring-red-200 ring-offset-2 ring-offset-red-200 focus-visible:border-red-400 focus-visible:ring-4 focus-visible:ring-red-200 focus-visible:ring-offset-2 focus-visible:ring-offset-red-200':
+                  userInputHasErrors,
+              })}
+              value={localText}
+              onChange={handleTextChange}
             />
           </div>
 
+          {parsedFieldMeta?.characterLimit !== undefined && parsedFieldMeta?.characterLimit > 0 && !userInputHasErrors && (
+            <div className="text-muted-foreground text-sm">
+              {charactersRemaining} characters remaining
+            </div>
+          )}
+
+          {userInputHasErrors && (
+            <div className="text-sm">
+              {errors.required.map((error, index) => (
+                <p key={index} className="text-red-500">
+                  {error}
+                </p>
+              ))}
+              {errors.characterLimit.map((error, index) => (
+                <p key={index} className="text-red-500">
+                  {error}{' '}
+                  {charactersRemaining < 0 && `(${Math.abs(charactersRemaining)} characters over)`}
+                </p>
+              ))}
+            </div>
+          )}
+
           <DialogFooter>
             <div className="mt-4 flex w-full flex-1 flex-nowrap gap-4">
               <Button
@@ -201,10 +318,10 @@ export const TextField = ({ field, recipient, onSignField, onUnsignField }: Text
               <Button
                 type="button"
                 className="flex-1"
-                disabled={!localText}
+                disabled={!localText || userInputHasErrors}
                 onClick={() => onDialogSignClick()}
               >
-                Save Text
+                Save
               </Button>
             </div>
           </DialogFooter>
diff --git a/apps/web/src/components/document/document-read-only-fields.tsx b/apps/web/src/components/document/document-read-only-fields.tsx
index d62210b72..d07c0b26c 100644
--- a/apps/web/src/components/document/document-read-only-fields.tsx
+++ b/apps/web/src/components/document/document-read-only-fields.tsx
@@ -42,12 +42,12 @@ export const DocumentReadOnlyFields = ({ documentMeta, fields }: DocumentReadOnl
             <FieldRootContainer
               field={field}
               key={field.id}
-              cardClassName="border-gray-100/50 !shadow-none backdrop-blur-[1px] bg-background/90"
+              cardClassName="border-gray-300/50 !shadow-none backdrop-blur-[1px] bg-gray-50 ring-0 ring-offset-0"
             >
               <div className="absolute -right-3 -top-3">
                 <PopoverHover
                   trigger={
-                    <Avatar className="dark:border-border h-8 w-8 border-2 border-solid border-gray-200/50 transition-colors hover:border-gray-200">
+                    <Avatar className="dark:border-foreground h-8 w-8 border-2 border-solid border-gray-200/50 transition-colors hover:border-gray-200">
                       <AvatarFallback className="bg-neutral-50 text-xs text-gray-400">
                         {extractInitials(field.Recipient.name || field.Recipient.email)}
                       </AvatarFallback>
@@ -78,7 +78,7 @@ export const DocumentReadOnlyFields = ({ documentMeta, fields }: DocumentReadOnl
                 </PopoverHover>
               </div>
 
-              <div className="text-muted-foreground break-all text-sm">
+              <div className="text-muted-foreground dark:text-background/70 break-all text-sm">
                 {field.Recipient.signingStatus === SigningStatus.SIGNED &&
                   match(field)
                     .with({ type: FieldType.SIGNATURE }, (field) =>
@@ -95,9 +95,19 @@ export const DocumentReadOnlyFields = ({ documentMeta, fields }: DocumentReadOnl
                       ),
                     )
                     .with(
-                      { type: P.union(FieldType.NAME, FieldType.TEXT, FieldType.EMAIL) },
+                      {
+                        type: P.union(
+                          FieldType.NAME,
+                          FieldType.EMAIL,
+                          FieldType.NUMBER,
+                          FieldType.RADIO,
+                          FieldType.CHECKBOX,
+                          FieldType.DROPDOWN,
+                        ),
+                      },
                       () => field.customText,
                     )
+                    .with({ type: FieldType.TEXT }, () => field.customText.substring(0, 20) + '...')
                     .with({ type: FieldType.DATE }, () =>
                       convertToLocalSystemFormat(
                         field.customText,
diff --git a/packages/api/v1/implementation.ts b/packages/api/v1/implementation.ts
index 5fb162dce..6bcd767e9 100644
--- a/packages/api/v1/implementation.ts
+++ b/packages/api/v1/implementation.ts
@@ -1034,6 +1034,8 @@ export const ApiContractV1Implementation = createNextRoute(ApiContractV1, {
     }
 
     const field = await getFieldById({
+      userId: user.id,
+      teamId: team?.id,
       fieldId: Number(fieldId),
       documentId: Number(documentId),
     }).catch(() => null);
diff --git a/packages/lib/advanced-fields-validation/validate-checkbox.ts b/packages/lib/advanced-fields-validation/validate-checkbox.ts
new file mode 100644
index 000000000..409c4fdd4
--- /dev/null
+++ b/packages/lib/advanced-fields-validation/validate-checkbox.ts
@@ -0,0 +1,82 @@
+import { checkboxValidationSigns } from '@documenso/ui/primitives/document-flow/field-items-advanced-settings/constants';
+
+interface CheckboxFieldMeta {
+  readOnly?: boolean;
+  required?: boolean;
+  validationRule?: string;
+  validationLength?: number;
+}
+
+export const validateCheckboxField = (
+  values: string[],
+  fieldMeta: CheckboxFieldMeta,
+  isSigningPage: boolean = false,
+): string[] => {
+  const errors = [];
+
+  const { readOnly, required, validationRule, validationLength } = fieldMeta;
+
+  if (readOnly && required) {
+    errors.push('A field cannot be both read-only and required');
+  }
+
+  if (values.length === 0) {
+    errors.push('At least one option must be added');
+  }
+
+  if (readOnly && values.length === 0) {
+    errors.push('A read-only field must have at least one value');
+  }
+
+  if (isSigningPage && required && values.length === 0) {
+    errors.push('Selecting an option is required');
+  }
+
+  if (validationRule && !validationLength) {
+    errors.push('You need to specify the number of options for validation');
+  }
+
+  if (validationLength && !validationRule) {
+    errors.push('You need to specify the validation rule');
+  }
+
+  if (validationRule && validationLength) {
+    const validation = checkboxValidationSigns.find((sign) => sign.label === validationRule);
+
+    if (validation) {
+      let lengthCondition = false;
+
+      switch (validation.value) {
+        case '=':
+          lengthCondition = isSigningPage
+            ? values.length !== validationLength
+            : values.length < validationLength;
+          break;
+        case '>=':
+          lengthCondition = values.length < validationLength;
+          break;
+        case '<=':
+          lengthCondition = isSigningPage
+            ? values.length > validationLength
+            : values.length < validationLength;
+          break;
+      }
+
+      if (lengthCondition) {
+        let errorMessage;
+        if (isSigningPage) {
+          errorMessage = `You need to ${validationRule.toLowerCase()} ${validationLength} options`;
+        } else {
+          errorMessage =
+            validation.value === '<='
+              ? `You need to select at least ${validationLength} options`
+              : `You need to add at least ${validationLength} options`;
+        }
+
+        errors.push(errorMessage);
+      }
+    }
+  }
+
+  return errors;
+};
diff --git a/packages/lib/advanced-fields-validation/validate-dropdown.ts b/packages/lib/advanced-fields-validation/validate-dropdown.ts
new file mode 100644
index 000000000..e49270fae
--- /dev/null
+++ b/packages/lib/advanced-fields-validation/validate-dropdown.ts
@@ -0,0 +1,54 @@
+interface DropdownFieldMeta {
+  readOnly?: boolean;
+  required?: boolean;
+  values?: { value: string }[];
+  defaultValue?: string;
+}
+
+export const validateDropdownField = (
+  value: string | undefined,
+  fieldMeta: DropdownFieldMeta,
+  isSigningPage: boolean = false,
+): string[] => {
+  const errors = [];
+
+  const { readOnly, required, values, defaultValue } = fieldMeta;
+
+  if (readOnly && required) {
+    errors.push('A field cannot be both read-only and required');
+  }
+
+  if (readOnly && (!values || values.length === 0)) {
+    errors.push('A read-only field must have at least one value');
+  }
+
+  if (isSigningPage && required && !value) {
+    errors.push('Choosing an option is required');
+  }
+
+  if (values && values.length === 0) {
+    errors.push('Select field must have at least one option');
+  }
+
+  if (values && values.length === 0 && defaultValue) {
+    errors.push('Default value must be one of the available options');
+  }
+
+  if (value && values && !values.find((item) => item.value === value)) {
+    errors.push('Selected value must be one of the available options');
+  }
+
+  if (values && defaultValue && !values.find((item) => item.value === defaultValue)) {
+    errors.push('Default value must be one of the available options');
+  }
+
+  if (values && values.some((item) => item.value.length < 1)) {
+    errors.push('Option value cannot be empty');
+  }
+
+  if (values && new Set(values.map((item) => item.value)).size !== values.length) {
+    errors.push('Duplicate values are not allowed');
+  }
+
+  return errors;
+};
diff --git a/packages/lib/advanced-fields-validation/validate-number.ts b/packages/lib/advanced-fields-validation/validate-number.ts
new file mode 100644
index 000000000..ec259fca5
--- /dev/null
+++ b/packages/lib/advanced-fields-validation/validate-number.ts
@@ -0,0 +1,67 @@
+// import { numberFormatValues } from '@documenso/ui/primitives/document-flow/field-items-advanced-settings/constants';
+
+interface NumberFieldMeta {
+  minValue?: number;
+  maxValue?: number;
+  readOnly?: boolean;
+  required?: boolean;
+  numberFormat?: string;
+}
+
+export const validateNumberField = (
+  value: string,
+  fieldMeta?: NumberFieldMeta,
+  isSigningPage: boolean = false,
+): string[] => {
+  const errors = [];
+
+  const { minValue, maxValue, readOnly, required, numberFormat } = fieldMeta || {};
+
+  const formatRegex: { [key: string]: RegExp } = {
+    '123,456,789.00': /^(?:\d{1,3}(?:,\d{3})*|\d+)(?:\.\d{1,2})?$/,
+    '123.456.789,00': /^(?:\d{1,3}(?:\.\d{3})*|\d+)(?:,\d{1,2})?$/,
+    '123456,789.00': /^(?:\d+)(?:,\d{1,3}(?:\.\d{1,2})?)?$/,
+  };
+
+  const isValidFormat = numberFormat ? formatRegex[numberFormat].test(value) : true;
+
+  if (!isValidFormat) {
+    errors.push(`Value ${value} does not match the number format - ${numberFormat}`);
+  }
+
+  const numberValue = parseFloat(value);
+
+  if (isSigningPage && required && !value) {
+    errors.push('Value is required');
+  }
+
+  if (!/^[0-9,.]+$/.test(value.trim())) {
+    errors.push(`Value is not a valid number`);
+  }
+
+  if (minValue !== undefined && minValue > 0 && numberValue < minValue) {
+    errors.push(`Value ${value} is less than the minimum value of ${minValue}`);
+  }
+
+  if (maxValue !== undefined && maxValue > 0 && numberValue > maxValue) {
+    errors.push(`Value ${value} is greater than the maximum value of ${maxValue}`);
+  }
+
+  if (minValue !== undefined && maxValue !== undefined && minValue > maxValue) {
+    errors.push('Minimum value cannot be greater than maximum value');
+  }
+
+  if (maxValue !== undefined && minValue !== undefined && maxValue < minValue) {
+    errors.push('Maximum value cannot be less than minimum value');
+  }
+
+  if (readOnly && numberValue < 1) {
+    errors.push('A read-only field must have a value greater than 0');
+  }
+
+  if (readOnly && required) {
+    errors.push('A field cannot be both read-only and required');
+  }
+
+  return errors;
+};
diff --git a/packages/lib/advanced-fields-validation/validate-radio.ts b/packages/lib/advanced-fields-validation/validate-radio.ts
new file mode 100644
index 000000000..36cafc8d2
--- /dev/null
+++ b/packages/lib/advanced-fields-validation/validate-radio.ts
@@ -0,0 +1,41 @@
+interface RadioFieldMeta {
+  readOnly?: boolean;
+  required?: boolean;
+  values?: { checked: boolean; value: string }[];
+}
+
+export const validateRadioField = (
+  value: string | undefined,
+  fieldMeta: RadioFieldMeta,
+  isSigningPage: boolean = false,
+): string[] => {
+  const errors = [];
+
+  const { readOnly, required, values } = fieldMeta;
+
+  if (readOnly && required) {
+    errors.push('A field cannot be both read-only and required');
+  }
+
+  if (readOnly && (!values || values.length === 0)) {
+    errors.push('A read-only field must have at least one value');
+  }
+
+  if (isSigningPage && required && !value) {
+    errors.push('Choosing an option is required');
+  }
+
+  if (values) {
+    const checkedRadioFieldValues = values.filter((option) => option.checked);
+
+    if (values.length === 0) {
+      errors.push('Radio field must have at least one option');
+    }
+
+    if (checkedRadioFieldValues.length > 1) {
+      errors.push('There cannot be more than one checked option');
+    }
+  }
+
+  return errors;
+};
diff --git a/packages/lib/advanced-fields-validation/validate-text.ts b/packages/lib/advanced-fields-validation/validate-text.ts
new file mode 100644
index 000000000..ae4215905
--- /dev/null
+++ b/packages/lib/advanced-fields-validation/validate-text.ts
@@ -0,0 +1,33 @@
+interface TextFieldMeta {
+  characterLimit?: number;
+  readOnly?: boolean;
+  required?: boolean;
+}
+
+export const validateTextField = (
+  value: string,
+  fieldMeta: TextFieldMeta,
+  isSigningPage: boolean = false,
+): string[] => {
+  const errors = [];
+
+  const { characterLimit, readOnly, required } = fieldMeta;
+
+  if (required && !value && isSigningPage) {
+    errors.push('Value is required');
+  }
+
+  if (characterLimit !== undefined && characterLimit > 0 && value.length > characterLimit) {
+    errors.push(`Value length (${value.length}) exceeds the character limit (${characterLimit})`);
+  }
+
+  if (readOnly && value.length < 1) {
+    errors.push('A read-only field must have text');
+  }
+
+  if (readOnly && required) {
+    errors.push('A field cannot be both read-only and required');
+  }
+
+  return errors;
+};
diff --git a/packages/lib/client-only/hooks/use-field-item-styles.ts b/packages/lib/client-only/hooks/use-field-item-styles.ts
new file mode 100644
index 000000000..747ad1db2
--- /dev/null
+++ b/packages/lib/client-only/hooks/use-field-item-styles.ts
@@ -0,0 +1,25 @@
+import { useMemo } from 'react';
+
+import type { CombinedStylesKey } from '../../../ui/primitives/document-flow/add-fields';
+import { combinedStyles } from '../../../ui/primitives/document-flow/field-item';
+
+const defaultFieldItemStyles = {
+  borderClass: 'border-field-card-border',
+  activeBorderClass: 'border-field-card-border/80',
+  initialsBGClass: 'text-field-card-foreground/50 bg-slate-900/10',
+  fieldBackground: 'bg-field-card-background',
+};
+
+export const useFieldItemStyles = (color: CombinedStylesKey | null) => {
+  return useMemo(() => {
+    if (!color) return defaultFieldItemStyles;
+
+    const selectedColorVariant = combinedStyles[color];
+    return {
+      activeBorderClass: selectedColorVariant?.borderActive,
+      borderClass: selectedColorVariant?.border,
+      initialsBGClass: selectedColorVariant?.initialsBG,
+      fieldBackground: selectedColorVariant?.fieldBackground,
+    };
+  }, [color]);
+};
diff --git a/packages/lib/server-only/document/seal-document.ts b/packages/lib/server-only/document/seal-document.ts
index fc8d753bf..b937b33ea 100644
--- a/packages/lib/server-only/document/seal-document.ts
+++ b/packages/lib/server-only/document/seal-document.ts
@@ -117,6 +117,9 @@ export const sealDocument = async ({
     await insertFieldInPDF(doc, field);
   }
 
+  // Re-flatten post-insertion to handle fields that create arcoFields
+  flattenForm(doc);
+
   const pdfBytes = await doc.save();
 
   const pdfBuffer = await signPdf({ pdf: Buffer.from(pdfBytes) });
diff --git a/packages/lib/server-only/document/send-document.tsx b/packages/lib/server-only/document/send-document.tsx
index ddc13ed5d..10ec3bc44 100644
--- a/packages/lib/server-only/document/send-document.tsx
+++ b/packages/lib/server-only/document/send-document.tsx
@@ -1,5 +1,4 @@
 import { sealDocument } from '@documenso/lib/server-only/document/seal-document';
-import { updateDocument } from '@documenso/lib/server-only/document/update-document';
 import { DOCUMENT_AUDIT_LOG_TYPE } from '@documenso/lib/types/document-audit-logs';
 import type { RequestMetadata } from '@documenso/lib/universal/extract-request-metadata';
 import { putPdfFile } from '@documenso/lib/universal/upload/put-file';
@@ -161,14 +160,7 @@ export const sendDocument = async ({
   );
 
   if (allRecipientsHaveNoActionToTake) {
-    const updatedDocument = await updateDocument({
-      documentId,
-      userId,
-      teamId,
-      data: { status: DocumentStatus.COMPLETED },
-    });
-
-    await sealDocument({ documentId: updatedDocument.id, requestMetadata });
+    await sealDocument({ documentId, requestMetadata });
 
     // Keep the return type the same for the `sendDocument` method
     return await prisma.document.findFirstOrThrow({
diff --git a/packages/lib/server-only/field/get-field-by-id.ts b/packages/lib/server-only/field/get-field-by-id.ts
index 0e0f9b2dd..71cebc95b 100644
--- a/packages/lib/server-only/field/get-field-by-id.ts
+++ b/packages/lib/server-only/field/get-field-by-id.ts
@@ -1,15 +1,47 @@
 import { prisma } from '@documenso/prisma';
 
 export type GetFieldByIdOptions = {
+  userId: number;
+  teamId?: number;
   fieldId: number;
-  documentId: number;
+  documentId?: number;
+  templateId?: number;
 };
 
-export const getFieldById = async ({ fieldId, documentId }: GetFieldByIdOptions) => {
+export const getFieldById = async ({
+  userId,
+  teamId,
+  fieldId,
+  documentId,
+  templateId,
+}: GetFieldByIdOptions) => {
   const field = await prisma.field.findFirst({
     where: {
       id: fieldId,
       documentId,
+      templateId,
+      Document: {
+        OR:
+          teamId === undefined
+            ? [
+                {
+                  userId,
+                  teamId: null,
+                },
+              ]
+            : [
+                {
+                  teamId,
+                  team: {
+                    members: {
+                      some: {
+                        userId,
+                      },
+                    },
+                  },
+                },
+              ],
+      },
     },
   });
 
diff --git a/packages/lib/server-only/field/set-fields-for-document.ts b/packages/lib/server-only/field/set-fields-for-document.ts
index a5b1cfd8b..da7ed105c 100644
--- a/packages/lib/server-only/field/set-fields-for-document.ts
+++ b/packages/lib/server-only/field/set-fields-for-document.ts
@@ -1,12 +1,26 @@
+import { validateCheckboxField } from '@documenso/lib/advanced-fields-validation/validate-checkbox';
+import { validateDropdownField } from '@documenso/lib/advanced-fields-validation/validate-dropdown';
+import { validateNumberField } from '@documenso/lib/advanced-fields-validation/validate-number';
+import { validateRadioField } from '@documenso/lib/advanced-fields-validation/validate-radio';
+import { validateTextField } from '@documenso/lib/advanced-fields-validation/validate-text';
 import { DOCUMENT_AUDIT_LOG_TYPE } from '@documenso/lib/types/document-audit-logs';
+import {
+  type TFieldMetaSchema as FieldMeta,
+  ZCheckboxFieldMeta,
+  ZDropdownFieldMeta,
+  ZFieldMetaSchema,
+  ZNumberFieldMeta,
+  ZRadioFieldMeta,
+  ZTextFieldMeta,
+} from '@documenso/lib/types/field-meta';
 import type { RequestMetadata } from '@documenso/lib/universal/extract-request-metadata';
 import {
   createDocumentAuditLogData,
   diffFieldChanges,
 } from '@documenso/lib/utils/document-audit-logs';
 import { prisma } from '@documenso/prisma';
-import type { Field, FieldType } from '@documenso/prisma/client';
-import { SendStatus, SigningStatus } from '@documenso/prisma/client';
+import type { Field } from '@documenso/prisma/client';
+import { FieldType, SendStatus, SigningStatus } from '@documenso/prisma/client';
 
 export interface SetFieldsForDocumentOptions {
   userId: number;
@@ -20,6 +34,7 @@ export interface SetFieldsForDocumentOptions {
     pageY: number;
     pageWidth: number;
     pageHeight: number;
+    fieldMeta?: FieldMeta;
   }[];
   requestMetadata?: RequestMetadata;
 }
@@ -103,6 +118,83 @@ export const setFieldsForDocument = async ({
       linkedFields.map(async (field) => {
         const fieldSignerEmail = field.signerEmail.toLowerCase();
 
+        const parsedFieldMeta = field.fieldMeta
+          ? ZFieldMetaSchema.parse(field.fieldMeta)
+          : undefined;
+
+        if (field.type === FieldType.TEXT && field.fieldMeta) {
+          const textFieldParsedMeta = ZTextFieldMeta.parse(field.fieldMeta);
+          const errors = validateTextField(textFieldParsedMeta.text || '', textFieldParsedMeta);
+
+          if (errors.length > 0) {
+            throw new Error(errors.join(', '));
+          }
+        }
+
+        if (field.type === FieldType.NUMBER && field.fieldMeta) {
+          const numberFieldParsedMeta = ZNumberFieldMeta.parse(field.fieldMeta);
+          const errors = validateNumberField(
+            String(numberFieldParsedMeta.value),
+            numberFieldParsedMeta,
+          );
+
+          if (errors.length > 0) {
+            throw new Error(errors.join(', '));
+          }
+        }
+
+        if (field.type === FieldType.CHECKBOX) {
+          if (field.fieldMeta) {
+            const checkboxFieldParsedMeta = ZCheckboxFieldMeta.parse(field.fieldMeta);
+            const errors = validateCheckboxField(
+              checkboxFieldParsedMeta?.values?.map((item) => item.value) ?? [],
+              checkboxFieldParsedMeta,
+            );
+
+            if (errors.length > 0) {
+              throw new Error(errors.join(', '));
+            }
+          } else {
+            throw new Error(
+              'To proceed further, please set at least one value for the Checkbox field',
+            );
+          }
+        }
+
+        if (field.type === FieldType.RADIO) {
+          if (field.fieldMeta) {
+            const radioFieldParsedMeta = ZRadioFieldMeta.parse(field.fieldMeta);
+            const checkedRadioFieldValue = radioFieldParsedMeta.values?.find(
+              (option) => option.checked,
+            )?.value;
+
+            const errors = validateRadioField(checkedRadioFieldValue, radioFieldParsedMeta);
+
+            if (errors.length > 0) {
+              throw new Error(errors.join('. '));
+            }
+          } else {
+            throw new Error(
+              'To proceed further, please set at least one value for the Radio field',
+            );
+          }
+        }
+
+        if (field.type === FieldType.DROPDOWN) {
+          if (field.fieldMeta) {
+            const dropdownFieldParsedMeta = ZDropdownFieldMeta.parse(field.fieldMeta);
+            const errors = validateDropdownField(undefined, dropdownFieldParsedMeta);
+
+            if (errors.length > 0) {
+              throw new Error(errors.join('. '));
+            }
+          } else {
+            throw new Error(
+              'To proceed further, please set at least one value for the Dropdown field',
+            );
+          }
+        }
+
         const upsertedField = await tx.field.upsert({
           where: {
             id: field._persisted?.id ?? -1,
@@ -114,6 +206,7 @@ export const setFieldsForDocument = async ({
             positionY: field.pageY,
             width: field.pageWidth,
             height: field.pageHeight,
+            fieldMeta: parsedFieldMeta,
           },
           create: {
             type: field.type,
@@ -124,6 +217,7 @@ export const setFieldsForDocument = async ({
             height: field.pageHeight,
             customText: '',
             inserted: false,
+            fieldMeta: parsedFieldMeta,
             Document: {
               connect: {
                 id: documentId,
diff --git a/packages/lib/server-only/field/set-fields-for-template.ts b/packages/lib/server-only/field/set-fields-for-template.ts
index 62e8cbcd1..c38d96b76 100644
--- a/packages/lib/server-only/field/set-fields-for-template.ts
+++ b/packages/lib/server-only/field/set-fields-for-template.ts
@@ -1,5 +1,19 @@
+import { validateCheckboxField } from '@documenso/lib/advanced-fields-validation/validate-checkbox';
+import { validateDropdownField } from '@documenso/lib/advanced-fields-validation/validate-dropdown';
+import { validateNumberField } from '@documenso/lib/advanced-fields-validation/validate-number';
+import { validateRadioField } from '@documenso/lib/advanced-fields-validation/validate-radio';
+import { validateTextField } from '@documenso/lib/advanced-fields-validation/validate-text';
+import {
+  type TFieldMetaSchema as FieldMeta,
+  ZCheckboxFieldMeta,
+  ZDropdownFieldMeta,
+  ZFieldMetaSchema,
+  ZNumberFieldMeta,
+  ZRadioFieldMeta,
+  ZTextFieldMeta,
+} from '@documenso/lib/types/field-meta';
 import { prisma } from '@documenso/prisma';
-import type { FieldType } from '@documenso/prisma/client';
+import { FieldType } from '@documenso/prisma/client';
 
 export type SetFieldsForTemplateOptions = {
   userId: number;
@@ -13,6 +27,7 @@ export type SetFieldsForTemplateOptions = {
     pageY: number;
     pageWidth: number;
     pageHeight: number;
+    fieldMeta?: FieldMeta;
   }[];
 };
 
@@ -70,8 +85,60 @@ export const setFieldsForTemplate = async ({
   const persistedFields = await prisma.$transaction(
     // Disabling as wrapping promises here causes type issues
     // eslint-disable-next-line @typescript-eslint/promise-function-async
-    linkedFields.map((field) =>
-      prisma.field.upsert({
+    linkedFields.map((field) => {
+      const parsedFieldMeta = field.fieldMeta ? ZFieldMetaSchema.parse(field.fieldMeta) : undefined;
+
+      if (field.type === FieldType.TEXT && field.fieldMeta) {
+        const textFieldParsedMeta = ZTextFieldMeta.parse(field.fieldMeta);
+        const errors = validateTextField(textFieldParsedMeta.text || '', textFieldParsedMeta);
+        if (errors.length > 0) {
+          throw new Error(errors.join(', '));
+        }
+      }
+
+      if (field.type === FieldType.NUMBER && field.fieldMeta) {
+        const numberFieldParsedMeta = ZNumberFieldMeta.parse(field.fieldMeta);
+        const errors = validateNumberField(
+          String(numberFieldParsedMeta.value),
+          numberFieldParsedMeta,
+        );
+        if (errors.length > 0) {
+          throw new Error(errors.join(', '));
+        }
+      }
+
+      if (field.type === FieldType.CHECKBOX && field.fieldMeta) {
+        const checkboxFieldParsedMeta = ZCheckboxFieldMeta.parse(field.fieldMeta);
+        const errors = validateCheckboxField(
+          checkboxFieldParsedMeta?.values?.map((item) => item.value) ?? [],
+          checkboxFieldParsedMeta,
+        );
+        if (errors.length > 0) {
+          throw new Error(errors.join(', '));
+        }
+      }
+
+      if (field.type === FieldType.RADIO && field.fieldMeta) {
+        const radioFieldParsedMeta = ZRadioFieldMeta.parse(field.fieldMeta);
+        const checkedRadioFieldValue = radioFieldParsedMeta.values?.find(
+          (option) => option.checked,
+        )?.value;
+        const errors = validateRadioField(checkedRadioFieldValue, radioFieldParsedMeta);
+        if (errors.length > 0) {
+          throw new Error(errors.join('. '));
+        }
+      }
+
+      if (field.type === FieldType.DROPDOWN && field.fieldMeta) {
+        const dropdownFieldParsedMeta = ZDropdownFieldMeta.parse(field.fieldMeta);
+        const errors = validateDropdownField(undefined, dropdownFieldParsedMeta);
+        if (errors.length > 0) {
+          throw new Error(errors.join('. '));
+        }
+      }
+
+      // Proceed with upsert operation
+      return prisma.field.upsert({
         where: {
           id: field._persisted?.id ?? -1,
           templateId,
@@ -82,6 +149,7 @@ export const setFieldsForTemplate = async ({
           positionY: field.pageY,
           width: field.pageWidth,
           height: field.pageHeight,
+          fieldMeta: parsedFieldMeta,
         },
         create: {
           type: field.type,
@@ -92,6 +160,7 @@ export const setFieldsForTemplate = async ({
           height: field.pageHeight,
           customText: '',
           inserted: false,
+          fieldMeta: parsedFieldMeta,
           Template: {
             connect: {
               id: templateId,
@@ -106,8 +175,8 @@ export const setFieldsForTemplate = async ({
             },
           },
         },
-      }),
-    ),
+      });
+    }),
   );
 
   if (removedFields.length > 0) {
diff --git a/packages/lib/server-only/field/sign-field-with-token.ts b/packages/lib/server-only/field/sign-field-with-token.ts
index 6f7bbb029..aa596dc37 100644
--- a/packages/lib/server-only/field/sign-field-with-token.ts
+++ b/packages/lib/server-only/field/sign-field-with-token.ts
@@ -3,6 +3,11 @@
 import { DateTime } from 'luxon';
 import { match } from 'ts-pattern';
 
+import { validateCheckboxField } from '@documenso/lib/advanced-fields-validation/validate-checkbox';
+import { validateDropdownField } from '@documenso/lib/advanced-fields-validation/validate-dropdown';
+import { validateNumberField } from '@documenso/lib/advanced-fields-validation/validate-number';
+import { validateRadioField } from '@documenso/lib/advanced-fields-validation/validate-radio';
+import { validateTextField } from '@documenso/lib/advanced-fields-validation/validate-text';
 import { prisma } from '@documenso/prisma';
 import { DocumentStatus, FieldType, SigningStatus } from '@documenso/prisma/client';
 
@@ -10,6 +15,13 @@ import { DEFAULT_DOCUMENT_DATE_FORMAT } from '../../constants/date-formats';
 import { DEFAULT_DOCUMENT_TIME_ZONE } from '../../constants/time-zones';
 import { DOCUMENT_AUDIT_LOG_TYPE } from '../../types/document-audit-logs';
 import type { TRecipientActionAuth } from '../../types/document-auth';
+import {
+  ZCheckboxFieldMeta,
+  ZDropdownFieldMeta,
+  ZNumberFieldMeta,
+  ZRadioFieldMeta,
+  ZTextFieldMeta,
+} from '../../types/field-meta';
 import type { RequestMetadata } from '../../universal/extract-request-metadata';
 import { createDocumentAuditLogData } from '../../utils/document-audit-logs';
 import { validateFieldAuth } from '../document/validate-field-auth';
@@ -87,6 +99,52 @@ export const signFieldWithToken = async ({
     throw new Error(`Field ${fieldId} has no recipientId`);
   }
 
+  if (field.type === FieldType.NUMBER && field.fieldMeta) {
+    const numberFieldParsedMeta = ZNumberFieldMeta.parse(field.fieldMeta);
+    const errors = validateNumberField(value, numberFieldParsedMeta, true);
+
+    if (errors.length > 0) {
+      throw new Error(errors.join(', '));
+    }
+  }
+
+  if (field.type === FieldType.TEXT && field.fieldMeta) {
+    const textFieldParsedMeta = ZTextFieldMeta.parse(field.fieldMeta);
+    const errors = validateTextField(value, textFieldParsedMeta, true);
+
+    if (errors.length > 0) {
+      throw new Error(errors.join(', '));
+    }
+  }
+
+  if (field.type === FieldType.CHECKBOX && field.fieldMeta) {
+    const checkboxFieldParsedMeta = ZCheckboxFieldMeta.parse(field.fieldMeta);
+    const checkboxFieldValues = value.split(',');
+    const errors = validateCheckboxField(checkboxFieldValues, checkboxFieldParsedMeta, true);
+
+    if (errors.length > 0) {
+      throw new Error(errors.join(', '));
+    }
+  }
+
+  if (field.type === FieldType.RADIO && field.fieldMeta) {
+    const radioFieldParsedMeta = ZRadioFieldMeta.parse(field.fieldMeta);
+    const errors = validateRadioField(value, radioFieldParsedMeta, true);
+
+    if (errors.length > 0) {
+      throw new Error(errors.join(', '));
+    }
+  }
+
+  if (field.type === FieldType.DROPDOWN && field.fieldMeta) {
+    const dropdownFieldParsedMeta = ZDropdownFieldMeta.parse(field.fieldMeta);
+    const errors = validateDropdownField(value, dropdownFieldParsedMeta, true);
+
+    if (errors.length > 0) {
+      throw new Error(errors.join(', '));
+    }
+  }
+
   const derivedRecipientActionAuth = await validateFieldAuth({
     documentAuthOptions: document.authOptions,
     recipient,
@@ -177,6 +235,16 @@ export const signFieldWithToken = async ({
               type,
               data: updatedField.customText,
             }))
+            .with(
+              FieldType.NUMBER,
+              FieldType.RADIO,
+              FieldType.CHECKBOX,
+              FieldType.DROPDOWN,
+              (type) => ({
+                type,
+                data: updatedField.customText,
+              }),
+            )
             .exhaustive(),
           fieldSecurity: derivedRecipientActionAuth
             ? {
diff --git a/packages/lib/server-only/field/update-field.ts b/packages/lib/server-only/field/update-field.ts
index 84358d245..a8e84d043 100644
--- a/packages/lib/server-only/field/update-field.ts
+++ b/packages/lib/server-only/field/update-field.ts
@@ -1,3 +1,4 @@
+import { type TFieldMetaSchema as FieldMeta } from '@documenso/lib/types/field-meta';
 import { prisma } from '@documenso/prisma';
 import type { FieldType, Team } from '@documenso/prisma/client';
 
@@ -18,6 +19,7 @@ export type UpdateFieldOptions = {
   pageWidth?: number;
   pageHeight?: number;
   requestMetadata?: RequestMetadata;
+  fieldMeta?: FieldMeta;
 };
 
 export const updateField = async ({
@@ -33,6 +35,7 @@ export const updateField = async ({
   pageWidth,
   pageHeight,
   requestMetadata,
+  fieldMeta,
 }: UpdateFieldOptions) => {
   const oldField = await prisma.field.findFirstOrThrow({
     where: {
@@ -71,6 +74,7 @@ export const updateField = async ({
         positionY: pageY,
         width: pageWidth,
         height: pageHeight,
+        fieldMeta,
       },
       include: {
         Recipient: true,
diff --git a/packages/lib/server-only/pdf/insert-field-in-pdf.ts b/packages/lib/server-only/pdf/insert-field-in-pdf.ts
index 964556c83..401e03b05 100644
--- a/packages/lib/server-only/pdf/insert-field-in-pdf.ts
+++ b/packages/lib/server-only/pdf/insert-field-in-pdf.ts
@@ -1,7 +1,7 @@
 // https://github.com/Hopding/pdf-lib/issues/20#issuecomment-412852821
 import fontkit from '@pdf-lib/fontkit';
 import { PDFDocument, RotationTypes, degrees, radiansToDegrees } from 'pdf-lib';
-import { match } from 'ts-pattern';
+import { P, match } from 'ts-pattern';
 
 import {
   DEFAULT_HANDWRITING_FONT_SIZE,
@@ -13,6 +13,8 @@ import { FieldType } from '@documenso/prisma/client';
 import { isSignatureFieldType } from '@documenso/prisma/guards/is-signature-field';
 import type { FieldWithSignature } from '@documenso/prisma/types/field-with-signature';
 
+import { ZCheckboxFieldMeta, ZRadioFieldMeta } from '../../types/field-meta';
+
 export const insertFieldInPDF = async (pdf: PDFDocument, field: FieldWithSignature) => {
   const fontCaveat = await fetch(process.env.FONT_CAVEAT_URI).then(async (res) =>
     res.arrayBuffer(),
@@ -77,86 +79,163 @@ export const insertFieldInPDF = async (pdf: PDFDocument, field: FieldWithSignatu
     await pdf.embedFont(fontCaveat);
   }
 
-  const isInsertingImage =
-    isSignatureField && typeof field.Signature?.signatureImageAsBase64 === 'string';
+  await match(field)
+    .with(
+      {
+        type: P.union(FieldType.SIGNATURE, FieldType.FREE_SIGNATURE),
+        Signature: { signatureImageAsBase64: P.string },
+      },
+      async (field) => {
+        const image = await pdf.embedPng(field.Signature?.signatureImageAsBase64 ?? '');
 
-  if (isSignatureField && isInsertingImage) {
-    const image = await pdf.embedPng(field.Signature?.signatureImageAsBase64 ?? '');
+        let imageWidth = image.width;
+        let imageHeight = image.height;
 
-    let imageWidth = image.width;
-    let imageHeight = image.height;
+        const scalingFactor = Math.min(fieldWidth / imageWidth, fieldHeight / imageHeight, 1);
 
-    const scalingFactor = Math.min(fieldWidth / imageWidth, fieldHeight / imageHeight, 1);
+        imageWidth = imageWidth * scalingFactor;
+        imageHeight = imageHeight * scalingFactor;
 
-    imageWidth = imageWidth * scalingFactor;
-    imageHeight = imageHeight * scalingFactor;
+        let imageX = fieldX + (fieldWidth - imageWidth) / 2;
+        let imageY = fieldY + (fieldHeight - imageHeight) / 2;
 
-    let imageX = fieldX + (fieldWidth - imageWidth) / 2;
-    let imageY = fieldY + (fieldHeight - imageHeight) / 2;
+        // Invert the Y axis since PDFs use a bottom-left coordinate system
+        imageY = pageHeight - imageY - imageHeight;
 
-    // Invert the Y axis since PDFs use a bottom-left coordinate system
-    imageY = pageHeight - imageY - imageHeight;
+        if (pageRotationInDegrees !== 0) {
+          const adjustedPosition = adjustPositionForRotation(
+            pageWidth,
+            pageHeight,
+            imageX,
+            imageY,
+            pageRotationInDegrees,
+          );
 
-    if (pageRotationInDegrees !== 0) {
-      const adjustedPosition = adjustPositionForRotation(
-        pageWidth,
-        pageHeight,
-        imageX,
-        imageY,
-        pageRotationInDegrees,
-      );
+          imageX = adjustedPosition.xPos;
+          imageY = adjustedPosition.yPos;
+        }
 
-      imageX = adjustedPosition.xPos;
-      imageY = adjustedPosition.yPos;
-    }
+        page.drawImage(image, {
+          x: imageX,
+          y: imageY,
+          width: imageWidth,
+          height: imageHeight,
+          rotate: degrees(pageRotationInDegrees),
+        });
+      },
+    )
+    .with({ type: FieldType.CHECKBOX }, (field) => {
+      const meta = ZCheckboxFieldMeta.safeParse(field.fieldMeta);
 
-    page.drawImage(image, {
-      x: imageX,
-      y: imageY,
-      width: imageWidth,
-      height: imageHeight,
-      rotate: degrees(pageRotationInDegrees),
+      if (!meta.success) {
+        console.error(meta.error);
+
+        throw new Error('Invalid checkbox field meta');
+      }
+
+      const selected = field.customText.split(',');
+
+      for (const [index, item] of (meta.data.values ?? []).entries()) {
+        const offsetY = index * 16;
+
+        const checkbox = pdf.getForm().createCheckBox(`checkbox.${field.secondaryId}.${index}`);
+
+        if (selected.includes(item.value)) {
+          checkbox.check();
+        }
+
+        page.drawText(item.value.includes('empty-value-') ? '' : item.value, {
+          x: fieldX + 16,
+          y: pageHeight - (fieldY + offsetY),
+          size: 12,
+          font,
+          rotate: degrees(pageRotationInDegrees),
+        });
+
+        checkbox.addToPage(page, {
+          x: fieldX,
+          y: pageHeight - (fieldY + offsetY),
+          height: 8,
+          width: 8,
+        });
+      }
+    })
+    .with({ type: FieldType.RADIO }, (field) => {
+      const meta = ZRadioFieldMeta.safeParse(field.fieldMeta);
+
+      if (!meta.success) {
+        console.error(meta.error);
+
+        throw new Error('Invalid radio field meta');
+      }
+
+      const selected = field.customText.split(',');
+
+      for (const [index, item] of (meta.data.values ?? []).entries()) {
+        const offsetY = index * 16;
+
+        const radio = pdf.getForm().createRadioGroup(`radio.${field.secondaryId}.${index}`);
+
+        page.drawText(item.value.includes('empty-value-') ? '' : item.value, {
+          x: fieldX + 16,
+          y: pageHeight - (fieldY + offsetY),
+          size: 12,
+          font,
+          rotate: degrees(pageRotationInDegrees),
+        });
+
+        radio.addOptionToPage(item.value, page, {
+          x: fieldX,
+          y: pageHeight - (fieldY + offsetY),
+          height: 8,
+          width: 8,
+        });
+
+        if (selected.includes(item.value)) {
+          radio.select(item.value);
+        }
+      }
+    })
+    .otherwise((field) => {
+      const longestLineInTextForWidth = field.customText
+        .split('\n')
+        .sort((a, b) => b.length - a.length)[0];
+
+      let textWidth = font.widthOfTextAtSize(longestLineInTextForWidth, fontSize);
+      const textHeight = font.heightAtSize(fontSize);
+
+      const scalingFactor = Math.min(fieldWidth / textWidth, fieldHeight / textHeight, 1);
+
+      fontSize = Math.max(Math.min(fontSize * scalingFactor, maxFontSize), minFontSize);
+      textWidth = font.widthOfTextAtSize(longestLineInTextForWidth, fontSize);
+
+      let textX = fieldX + (fieldWidth - textWidth) / 2;
+      let textY = fieldY + (fieldHeight - textHeight) / 2;
+
+      // Invert the Y axis since PDFs use a bottom-left coordinate system
+      textY = pageHeight - textY - textHeight;
+
+      if (pageRotationInDegrees !== 0) {
+        const adjustedPosition = adjustPositionForRotation(
+          pageWidth,
+          pageHeight,
+          textX,
+          textY,
+          pageRotationInDegrees,
+        );
+
+        textX = adjustedPosition.xPos;
+        textY = adjustedPosition.yPos;
+      }
+
+      page.drawText(field.customText, {
+        x: textX,
+        y: textY,
+        size: fontSize,
+        font,
+        rotate: degrees(pageRotationInDegrees),
+      });
     });
-  } else {
-    const longestLineInTextForWidth = field.customText
-      .split('\n')
-      .sort((a, b) => b.length - a.length)[0];
-
-    let textWidth = font.widthOfTextAtSize(longestLineInTextForWidth, fontSize);
-    const textHeight = font.heightAtSize(fontSize);
-
-    const scalingFactor = Math.min(fieldWidth / textWidth, fieldHeight / textHeight, 1);
-
-    fontSize = Math.max(Math.min(fontSize * scalingFactor, maxFontSize), minFontSize);
-    textWidth = font.widthOfTextAtSize(longestLineInTextForWidth, fontSize);
-
-    let textX = fieldX + (fieldWidth - textWidth) / 2;
-    let textY = fieldY + (fieldHeight - textHeight) / 2;
-
-    // Invert the Y axis since PDFs use a bottom-left coordinate system
-    textY = pageHeight - textY - textHeight;
-
-    if (pageRotationInDegrees !== 0) {
-      const adjustedPosition = adjustPositionForRotation(
-        pageWidth,
-        pageHeight,
-        textX,
-        textY,
-        pageRotationInDegrees,
-      );
-
-      textX = adjustedPosition.xPos;
-      textY = adjustedPosition.yPos;
-    }
-
-    page.drawText(field.customText, {
-      x: textX,
-      y: textY,
-      size: fontSize,
-      font,
-      rotate: degrees(pageRotationInDegrees),
-    });
-  }
 
   return pdf;
 };
diff --git a/packages/lib/server-only/template/create-document-from-direct-template.ts b/packages/lib/server-only/template/create-document-from-direct-template.ts
index 494307e9b..e7f119dfa 100644
--- a/packages/lib/server-only/template/create-document-from-direct-template.ts
+++ b/packages/lib/server-only/template/create-document-from-direct-template.ts
@@ -13,6 +13,7 @@ import {
   DocumentSource,
   DocumentStatus,
   FieldType,
+  Prisma,
   RecipientRole,
   SendStatus,
   SigningStatus,
@@ -26,6 +27,7 @@ import { AppError, AppErrorCode } from '../../errors/app-error';
 import { DOCUMENT_AUDIT_LOG_TYPE } from '../../types/document-audit-logs';
 import type { TRecipientActionAuthTypes } from '../../types/document-auth';
 import { DocumentAccessAuth, ZRecipientAuthOptionsSchema } from '../../types/document-auth';
+import { ZFieldMetaSchema } from '../../types/field-meta';
 import type { RequestMetadata } from '../../universal/extract-request-metadata';
 import type { CreateDocumentAuditLogDataResponse } from '../../utils/document-audit-logs';
 import { createDocumentAuditLogData } from '../../utils/document-audit-logs';
@@ -296,12 +298,16 @@ export const createDocumentFromDirectTemplate = async ({
           height: field.height,
           customText: '',
           inserted: false,
+          fieldMeta: field.fieldMeta,
         })),
       );
     });
 
     await tx.field.createMany({
-      data: nonDirectRecipientFieldsToCreate,
+      data: nonDirectRecipientFieldsToCreate.map((field) => ({
+        ...field,
+        fieldMeta: field.fieldMeta ? ZFieldMetaSchema.parse(field.fieldMeta) : undefined,
+      })),
     });
 
     // Create the direct recipient and their non signature fields.
@@ -331,6 +337,7 @@ export const createDocumentFromDirectTemplate = async ({
               height: templateField.height,
               customText,
               inserted: true,
+              fieldMeta: templateField.fieldMeta || Prisma.JsonNull,
             })),
           },
         },
@@ -361,6 +368,7 @@ export const createDocumentFromDirectTemplate = async ({
               height: templateField.height,
               customText: '',
               inserted: true,
+              fieldMeta: templateField.fieldMeta || Prisma.JsonNull,
               Signature: {
                 create: {
                   recipientId: createdDirectRecipient.id,
@@ -454,10 +462,20 @@ export const createDocumentFromDirectTemplate = async ({
                 data:
                   field.Signature?.signatureImageAsBase64 || field.Signature?.typedSignature || '',
               }))
-              .with(FieldType.DATE, FieldType.EMAIL, FieldType.NAME, FieldType.TEXT, (type) => ({
-                type,
-                data: field.customText,
-              }))
+              .with(
+                FieldType.DATE,
+                FieldType.EMAIL,
+                FieldType.NAME,
+                FieldType.TEXT,
+                FieldType.NUMBER,
+                FieldType.CHECKBOX,
+                FieldType.DROPDOWN,
+                FieldType.RADIO,
+                (type) => ({
+                  type,
+                  data: field.customText,
+                }),
+              )
               .exhaustive(),
             fieldSecurity: derivedRecipientActionAuth
               ? {
diff --git a/packages/lib/server-only/template/create-document-from-template.ts b/packages/lib/server-only/template/create-document-from-template.ts
index df7a768a0..879c1e1ca 100644
--- a/packages/lib/server-only/template/create-document-from-template.ts
+++ b/packages/lib/server-only/template/create-document-from-template.ts
@@ -13,6 +13,7 @@ import {
 import { AppError, AppErrorCode } from '../../errors/app-error';
 import { DOCUMENT_AUDIT_LOG_TYPE } from '../../types/document-audit-logs';
 import { ZRecipientAuthOptionsSchema } from '../../types/document-auth';
+import { ZFieldMetaSchema } from '../../types/field-meta';
 import type { RequestMetadata } from '../../universal/extract-request-metadata';
 import { createDocumentAuditLogData } from '../../utils/document-audit-logs';
 import {
@@ -225,12 +226,16 @@ export const createDocumentFromTemplate = async ({
           height: field.height,
           customText: '',
           inserted: false,
+          fieldMeta: field.fieldMeta,
         })),
       );
     });
 
     await tx.field.createMany({
-      data: fieldsToCreate,
+      data: fieldsToCreate.map((field) => ({
+        ...field,
+        fieldMeta: field.fieldMeta ? ZFieldMetaSchema.parse(field.fieldMeta) : undefined,
+      })),
     });
 
     await tx.documentAuditLog.create({
diff --git a/packages/lib/types/document-audit-logs.ts b/packages/lib/types/document-audit-logs.ts
index 63904c7f1..1d2bf7c53 100644
--- a/packages/lib/types/document-audit-logs.ts
+++ b/packages/lib/types/document-audit-logs.ts
@@ -253,6 +253,22 @@ export const ZDocumentAuditLogEventDocumentFieldInsertedSchema = z.object({
         type: z.union([z.literal(FieldType.SIGNATURE), z.literal(FieldType.FREE_SIGNATURE)]),
         data: z.string(),
       }),
+      z.object({
+        type: z.literal(FieldType.RADIO),
+        data: z.string(),
+      }),
+      z.object({
+        type: z.literal(FieldType.CHECKBOX),
+        data: z.string(),
+      }),
+      z.object({
+        type: z.literal(FieldType.DROPDOWN),
+        data: z.string(),
+      }),
+      z.object({
+        type: z.literal(FieldType.NUMBER),
+        data: z.string(),
+      }),
     ]),
     fieldSecurity: z.preprocess(
       (input) => {
diff --git a/packages/lib/types/field-meta.ts b/packages/lib/types/field-meta.ts
new file mode 100644
index 000000000..6ae1065c3
--- /dev/null
+++ b/packages/lib/types/field-meta.ts
@@ -0,0 +1,80 @@
+import { z } from 'zod';
+
+export const ZBaseFieldMeta = z.object({
+  label: z.string().optional(),
+  placeholder: z.string().optional(),
+  required: z.boolean().optional(),
+  readOnly: z.boolean().optional(),
+});
+
+export type TBaseFieldMeta = z.infer<typeof ZBaseFieldMeta>;
+
+export const ZTextFieldMeta = ZBaseFieldMeta.extend({
+  type: z.literal('text').default('text'),
+  text: z.string().optional(),
+  characterLimit: z.number().optional(),
+});
+
+export type TTextFieldMeta = z.infer<typeof ZTextFieldMeta>;
+
+export const ZNumberFieldMeta = ZBaseFieldMeta.extend({
+  type: z.literal('number').default('number'),
+  numberFormat: z.string().optional(),
+  value: z.string().optional(),
+  minValue: z.number().optional(),
+  maxValue: z.number().optional(),
+});
+
+export type TNumberFieldMeta = z.infer<typeof ZNumberFieldMeta>;
+
+export const ZRadioFieldMeta = ZBaseFieldMeta.extend({
+  type: z.literal('radio').default('radio'),
+  values: z
+    .array(
+      z.object({
+        id: z.number(),
+        checked: z.boolean(),
+        value: z.string(),
+      }),
+    )
+    .optional(),
+});
+
+export type TRadioFieldMeta = z.infer<typeof ZRadioFieldMeta>;
+
+export const ZCheckboxFieldMeta = ZBaseFieldMeta.extend({
+  type: z.literal('checkbox').default('checkbox'),
+  values: z
+    .array(
+      z.object({
+        id: z.number(),
+        checked: z.boolean(),
+        value: z.string(),
+      }),
+    )
+    .optional(),
+  validationRule: z.string().optional(),
+  validationLength: z.number().optional(),
+});
+
+export type TCheckboxFieldMeta = z.infer<typeof ZCheckboxFieldMeta>;
+
+export const ZDropdownFieldMeta = ZBaseFieldMeta.extend({
+  type: z.literal('dropdown').default('dropdown'),
+  values: z.array(z.object({ value: z.string() })).optional(),
+  defaultValue: z.string().optional(),
+});
+
+export type TDropdownFieldMeta = z.infer<typeof ZDropdownFieldMeta>;
+
+export const ZFieldMetaSchema = z
+  .union([
+    ZTextFieldMeta,
+    ZNumberFieldMeta,
+    ZRadioFieldMeta,
+    ZCheckboxFieldMeta,
+    ZDropdownFieldMeta,
+  ])
+  .optional();
+
+export type TFieldMetaSchema = z.infer<typeof ZFieldMetaSchema>;
diff --git a/packages/lib/utils/fields.ts b/packages/lib/utils/fields.ts
index b88fed3e9..beb65c5ad 100644
--- a/packages/lib/utils/fields.ts
+++ b/packages/lib/utils/fields.ts
@@ -1,4 +1,4 @@
-import { Field } from '@documenso/prisma/client';
+import type { Field } from '@documenso/prisma/client';
 
 /**
  * Sort the fields by the Y position on the document.
diff --git a/packages/prisma/migrations/20240503072448_add_more_field_types/migration.sql b/packages/prisma/migrations/20240503072448_add_more_field_types/migration.sql
new file mode 100644
index 000000000..94ddbcf3c
--- /dev/null
+++ b/packages/prisma/migrations/20240503072448_add_more_field_types/migration.sql
@@ -0,0 +1,12 @@
+-- AlterEnum
+-- This migration adds more than one value to an enum.
+-- With PostgreSQL versions 11 and earlier, this is not possible
+-- in a single migration. This can be worked around by creating
+-- multiple migrations, each migration adding only one value to
+-- the enum.
+
+
+ALTER TYPE "FieldType" ADD VALUE 'NUMBER';
+ALTER TYPE "FieldType" ADD VALUE 'RADIO';
+ALTER TYPE "FieldType" ADD VALUE 'CHECKBOX';
+ALTER TYPE "FieldType" ADD VALUE 'DROPDOWN';
diff --git a/packages/prisma/migrations/20240507131804_add_field_meta_for_advanced_fields/migration.sql b/packages/prisma/migrations/20240507131804_add_field_meta_for_advanced_fields/migration.sql
new file mode 100644
index 000000000..96a8e1bc4
--- /dev/null
+++ b/packages/prisma/migrations/20240507131804_add_field_meta_for_advanced_fields/migration.sql
@@ -0,0 +1,2 @@
+-- AlterTable
+ALTER TABLE "Field" ADD COLUMN     "fieldMeta" JSONB;
diff --git a/packages/prisma/schema.prisma b/packages/prisma/schema.prisma
index 3cb341a52..b48dcb1cb 100644
--- a/packages/prisma/schema.prisma
+++ b/packages/prisma/schema.prisma
@@ -413,6 +413,10 @@ enum FieldType {
   EMAIL
   DATE
   TEXT
+  NUMBER
+  RADIO
+  CHECKBOX
+  DROPDOWN
 }
 
 model Field {
@@ -433,6 +437,7 @@ model Field {
   Template    Template?  @relation(fields: [templateId], references: [id], onDelete: Cascade)
   Recipient   Recipient  @relation(fields: [recipientId], references: [id], onDelete: Cascade)
   Signature   Signature?
+  fieldMeta   Json?
 
   @@index([documentId])
   @@index([templateId])
diff --git a/packages/prisma/types/field-with-signature-and-fieldmeta.ts b/packages/prisma/types/field-with-signature-and-fieldmeta.ts
new file mode 100644
index 000000000..7bce5d9fe
--- /dev/null
+++ b/packages/prisma/types/field-with-signature-and-fieldmeta.ts
@@ -0,0 +1,7 @@
+import { type TFieldMetaSchema as FieldMeta } from '@documenso/lib/types/field-meta';
+import type { Field, Signature } from '@documenso/prisma/client';
+
+export type FieldWithSignatureAndFieldMeta = Field & {
+  Signature?: Signature | null;
+  fieldMeta: FieldMeta | null;
+};
diff --git a/packages/trpc/server/field-router/router.ts b/packages/trpc/server/field-router/router.ts
index d097e2400..2c9b06802 100644
--- a/packages/trpc/server/field-router/router.ts
+++ b/packages/trpc/server/field-router/router.ts
@@ -1,6 +1,7 @@
 import { TRPCError } from '@trpc/server';
 
 import { AppError } from '@documenso/lib/errors/app-error';
+import { getFieldById } from '@documenso/lib/server-only/field/get-field-by-id';
 import { removeSignedFieldWithToken } from '@documenso/lib/server-only/field/remove-signed-field-with-token';
 import { setFieldsForDocument } from '@documenso/lib/server-only/field/set-fields-for-document';
 import { setFieldsForTemplate } from '@documenso/lib/server-only/field/set-fields-for-template';
@@ -11,6 +12,7 @@ import { authenticatedProcedure, procedure, router } from '../trpc';
 import {
   ZAddFieldsMutationSchema,
   ZAddTemplateFieldsMutationSchema,
+  ZGetFieldQuerySchema,
   ZRemovedSignedFieldWithTokenMutationSchema,
   ZSignFieldWithTokenMutationSchema,
 } from './schema';
@@ -34,6 +36,7 @@ export const fieldRouter = router({
             pageY: field.pageY,
             pageWidth: field.pageWidth,
             pageHeight: field.pageHeight,
+            fieldMeta: field.fieldMeta,
           })),
           requestMetadata: extractNextApiRequestMetadata(ctx.req),
         });
@@ -65,6 +68,7 @@ export const fieldRouter = router({
             pageY: field.pageY,
             pageWidth: field.pageWidth,
             pageHeight: field.pageHeight,
+            fieldMeta: field.fieldMeta,
           })),
         });
       } catch (err) {
@@ -116,4 +120,49 @@ export const fieldRouter = router({
         });
       }
     }),
+
+  getField: authenticatedProcedure.input(ZGetFieldQuerySchema).query(async ({ input, ctx }) => {
+    try {
+      const { fieldId, teamId } = input;
+
+      return await getFieldById({
+        userId: ctx.user.id,
+        teamId,
+        fieldId,
+      });
+    } catch (err) {
+      console.error(err);
+
+      throw new TRPCError({
+        code: 'BAD_REQUEST',
+        message: 'We were unable to find this field. Please try again.',
+      });
+    }
+  }),
+
+  // This doesn't appear to be used anywhere, and it doesn't seem to support updating template fields
+  // so commenting this out for now.
+  // updateField: authenticatedProcedure
+  //   .input(ZUpdateFieldMutationSchema)
+  //   .mutation(async ({ input, ctx }) => {
+  //     try {
+  //       const { documentId, fieldId, fieldMeta, teamId } = input;
+
+  //       return await updateField({
+  //         userId: ctx.user.id,
+  //         teamId,
+  //         fieldId,
+  //         documentId,
+  //         requestMetadata: extractNextApiRequestMetadata(ctx.req),
+  //         fieldMeta: fieldMeta,
+  //       });
+  //     } catch (err) {
+  //       console.error(err);
+
+  //       throw new TRPCError({
+  //         code: 'BAD_REQUEST',
+  //         message: 'We were unable to set this field. Please try again later.',
+  //       });
+  //     }
+  //   }),
 });
diff --git a/packages/trpc/server/field-router/schema.ts b/packages/trpc/server/field-router/schema.ts
index eaf5d5bc8..4f408fc2c 100644
--- a/packages/trpc/server/field-router/schema.ts
+++ b/packages/trpc/server/field-router/schema.ts
@@ -1,6 +1,7 @@
 import { z } from 'zod';
 
 import { ZRecipientActionAuthSchema } from '@documenso/lib/types/document-auth';
+import { ZFieldMetaSchema } from '@documenso/lib/types/field-meta';
 import { FieldType } from '@documenso/prisma/client';
 
 export const ZAddFieldsMutationSchema = z.object({
@@ -16,6 +17,7 @@ export const ZAddFieldsMutationSchema = z.object({
       pageY: z.number().min(0),
       pageWidth: z.number().min(0),
       pageHeight: z.number().min(0),
+      fieldMeta: ZFieldMetaSchema,
     }),
   ),
 });
@@ -35,6 +37,7 @@ export const ZAddTemplateFieldsMutationSchema = z.object({
       pageY: z.number().min(0),
       pageWidth: z.number().min(0),
       pageHeight: z.number().min(0),
+      fieldMeta: ZFieldMetaSchema,
     }),
   ),
 });
@@ -59,3 +62,17 @@ export const ZRemovedSignedFieldWithTokenMutationSchema = z.object({
 export type TRemovedSignedFieldWithTokenMutationSchema = z.infer<
   typeof ZRemovedSignedFieldWithTokenMutationSchema
 >;
+
+export const ZGetFieldQuerySchema = z.object({
+  fieldId: z.number(),
+  teamId: z.number().optional(),
+});
+
+export type TGetFieldQuerySchema = z.infer<typeof ZGetFieldQuerySchema>;
+
+export const ZUpdateFieldMutationSchema = z.object({
+  fieldId: z.number(),
+  documentId: z.number(),
+  fieldMeta: ZFieldMetaSchema,
+  teamId: z.number().optional(),
+});
diff --git a/packages/trpc/server/singleplayer-router/helper.ts b/packages/trpc/server/singleplayer-router/helper.ts
index 32d03c0ac..8fa2f99c2 100644
--- a/packages/trpc/server/singleplayer-router/helper.ts
+++ b/packages/trpc/server/singleplayer-router/helper.ts
@@ -23,6 +23,10 @@ export const mapField = (
     .with(FieldType.EMAIL, () => signer.email)
     .with(FieldType.NAME, () => signer.name)
     .with(FieldType.TEXT, () => signer.customText)
+    .with(FieldType.NUMBER, () => signer.customText)
+    .with(FieldType.RADIO, () => signer.customText)
+    .with(FieldType.CHECKBOX, () => signer.customText)
+    .with(FieldType.DROPDOWN, () => signer.customText)
     .otherwise(() => '');
 
   return {
diff --git a/packages/trpc/server/singleplayer-router/router.ts b/packages/trpc/server/singleplayer-router/router.ts
index 1df83b405..6e8533c32 100644
--- a/packages/trpc/server/singleplayer-router/router.ts
+++ b/packages/trpc/server/singleplayer-router/router.ts
@@ -31,7 +31,7 @@ export const singleplayerRouter = router({
     .input(ZCreateSinglePlayerDocumentMutationSchema)
     .mutation(async ({ input }) => {
       try {
-        const { signer, fields, documentData, documentName } = input;
+        const { signer, fields, documentData, documentName, fieldMeta } = input;
 
         const document = await getFile({
           data: documentData.data,
@@ -69,6 +69,7 @@ export const singleplayerRouter = router({
             documentId: -1,
             templateId: null,
             recipientId: -1,
+            fieldMeta: fieldMeta || null,
           });
         }
 
diff --git a/packages/trpc/server/singleplayer-router/schema.ts b/packages/trpc/server/singleplayer-router/schema.ts
index 412429fca..bd03efbaf 100644
--- a/packages/trpc/server/singleplayer-router/schema.ts
+++ b/packages/trpc/server/singleplayer-router/schema.ts
@@ -1,5 +1,6 @@
 import { z } from 'zod';
 
+import { ZFieldMetaSchema } from '@documenso/lib/types/field-meta';
 import { DocumentDataType, FieldType } from '@documenso/prisma/client';
 
 export const ZCreateSinglePlayerDocumentMutationSchema = z.object({
@@ -24,6 +25,7 @@ export const ZCreateSinglePlayerDocumentMutationSchema = z.object({
       height: z.number(),
     }),
   ),
+  fieldMeta: ZFieldMetaSchema,
 });
 
 export type TCreateSinglePlayerDocumentMutationSchema = z.infer<
diff --git a/packages/ui/components/field/field.tsx b/packages/ui/components/field/field.tsx
index ce62443de..d6553947c 100644
--- a/packages/ui/components/field/field.tsx
+++ b/packages/ui/components/field/field.tsx
@@ -1,10 +1,12 @@
 'use client';
 
-import React, { useEffect, useState } from 'react';
+import React, { useEffect, useMemo, useState } from 'react';
 
 import { createPortal } from 'react-dom';
 
 import { useFieldPageCoords } from '@documenso/lib/client-only/hooks/use-field-page-coords';
+import type { TFieldMetaSchema } from '@documenso/lib/types/field-meta';
+import { ZFieldMetaSchema } from '@documenso/lib/types/field-meta';
 import type { Field } from '@documenso/prisma/client';
 
 import { cn } from '../../lib/utils';
@@ -22,6 +24,51 @@ export type FieldContainerPortalProps = {
   cardClassName?: string;
 };
 
+const getCardClassNames = (
+  field: Field,
+  parsedField: TFieldMetaSchema | null,
+  isValidating: boolean,
+  checkBoxOrRadio: boolean,
+  cardClassName?: string,
+) => {
+  const baseClasses = 'field-card-container relative z-20 h-full w-full transition-all';
+
+  const insertedClasses =
+    'bg-documenso/20 border-documenso ring-documenso-200 ring-offset-documenso-200 ring-2 ring-offset-2 dark:shadow-none';
+  const nonRequiredClasses =
+    'border-yellow-300 shadow-none ring-2 ring-yellow-100 ring-offset-2 ring-offset-yellow-100 dark:border-2';
+  const validatingClasses = 'border-orange-300 ring-1 ring-orange-300';
+  const requiredClasses =
+    'border-red-500 shadow-none ring-2 ring-red-200 ring-offset-2 ring-offset-red-200 hover:text-red-500';
+  const requiredCheckboxRadioClasses = 'border-dashed border-red-500';
+
+  if (checkBoxOrRadio) {
+    return cn(
+      {
+        [insertedClasses]: field.inserted,
+        'ring-offset-yellow-200 border-dashed border-yellow-300 ring-2 ring-yellow-200 ring-offset-2 dark:shadow-none':
+          !field.inserted && !parsedField?.required,
+        'shadow-none': !field.inserted,
+        [validatingClasses]: !field.inserted && isValidating,
+        [requiredCheckboxRadioClasses]: !field.inserted && parsedField?.required,
+      },
+      cardClassName,
+    );
+  }
+
+  return cn(
+    baseClasses,
+    {
+      [insertedClasses]: field.inserted,
+      [nonRequiredClasses]: !field.inserted && !parsedField?.required,
+      'shadow-none': !field.inserted && checkBoxOrRadio,
+      [validatingClasses]: !field.inserted && isValidating,
+      [requiredClasses]: !field.inserted && parsedField?.required && !checkBoxOrRadio,
+    },
+    cardClassName,
+  );
+};
+
 export function FieldContainerPortal({
   field,
   children,
@@ -29,16 +76,22 @@ export function FieldContainerPortal({
 }: FieldContainerPortalProps) {
   const coords = useFieldPageCoords(field);
 
+  const isCheckboxOrRadioField = field.type === 'CHECKBOX' || field.type === 'RADIO';
+  const isFieldSigned = field.inserted;
+
+  const style = {
+    top: `${coords.y}px`,
+    left: `${coords.x}px`,
+    // height: `${coords.height}px`,
+    // width: `${coords.width}px`,
+    ...((!isCheckboxOrRadioField) && {
+      height: `${coords.height}px`,
+      width: `${coords.width}px`,
+    }),
+  };
+
   return createPortal(
-    <div
-      className={cn('absolute', className)}
-      style={{
-        top: `${coords.y}px`,
-        left: `${coords.x}px`,
-        height: `${coords.height}px`,
-        width: `${coords.width}px`,
-      }}
-    >
+    <div className={cn('absolute', className)} style={style}>
       {children}
     </div>,
     document.body,
@@ -47,7 +100,6 @@ export function FieldContainerPortal({
 
 export function FieldRootContainer({ field, children, cardClassName }: FieldContainerPortalProps) {
   const [isValidating, setIsValidating] = useState(false);
-
   const ref = React.useRef<HTMLDivElement>(null);
 
   useEffect(() => {
@@ -70,19 +122,27 @@ export function FieldRootContainer({ field, children, cardClassName }: FieldCont
     };
   }, []);
 
+  const parsedField = useMemo(
+    () => (field.fieldMeta ? ZFieldMetaSchema.parse(field.fieldMeta) : null),
+    [field.fieldMeta],
+  );
+  const isCheckboxOrRadio = useMemo(
+    () => parsedField?.type === 'checkbox' || parsedField?.type === 'radio',
+    [parsedField],
+  );
+
+  const cardClassNames = useMemo(
+    () => getCardClassNames(field, parsedField, isValidating, isCheckboxOrRadio, cardClassName),
+    [field, parsedField, isValidating, isCheckboxOrRadio, cardClassName],
+  );
+
   return (
     <FieldContainerPortal field={field}>
       <Card
         id={`field-${field.id}`}
-        className={cn(
-          'field-card-container bg-background relative z-20 h-full w-full transition-all',
-          {
-            'border-orange-300 ring-1 ring-orange-300': !field.inserted && isValidating,
-          },
-          cardClassName,
-        )}
         ref={ref}
         data-inserted={field.inserted ? 'true' : 'false'}
+        className={cardClassNames}
       >
         <CardContent className="text-foreground hover:shadow-primary-foreground group flex h-full w-full flex-col items-center justify-center p-2">
           {children}
diff --git a/packages/ui/lib/signer-colors.ts b/packages/ui/lib/signer-colors.ts
new file mode 100644
index 000000000..862b75e58
--- /dev/null
+++ b/packages/ui/lib/signer-colors.ts
@@ -0,0 +1,108 @@
+// !: We declare all of our classes here since TailwindCSS will remove any unused CSS classes,
+// !: therefore doing this at runtime is not possible without whitelisting a set of classnames.
+// !:
+// !: This will later be improved as we move to a CSS variable approach and rotate the lightness
+// !: values of the declared variable to do all the background, border and shadow styles.
+export const SIGNER_COLOR_STYLES = {
+  green: {
+    default: {
+      background: 'bg-[hsl(var(--signer-green))]',
+      base: 'rounded-lg shadow-[0_0_0_5px_hsl(var(--signer-green)/10%),0_0_0_2px_hsl(var(--signer-green)/60%),0_0_0_0.5px_hsl(var(--signer-green))]',
+      fieldItem:
+        'group/field-item p-2 border-none ring-none hover:bg-gradient-to-r hover:from-[hsl(var(--signer-green))]/10 hover:to-[hsl(var(--signer-green))]/10',
+      fieldItemInitials:
+        'opacity-0 transition duration-200 group-hover/field-item:opacity-100 group-hover/field-item:bg-[hsl(var(--signer-green))]',
+      comboxBoxItem:
+        'hover:bg-[hsl(var(--signer-green)/15%)] active:bg-[hsl(var(--signer-green)/15%)]',
+    },
+  },
+
+  blue: {
+    default: {
+      background: 'bg-[hsl(var(--signer-blue))]',
+      base: 'rounded-lg shadow-[0_0_0_5px_hsl(var(--signer-blue)/10%),0_0_0_2px_hsl(var(--signer-blue)/60%),0_0_0_0.5px_hsl(var(--signer-blue))]',
+      fieldItem:
+        'group/field-item p-2 border-none ring-none hover:bg-gradient-to-r hover:from-[hsl(var(--signer-blue))]/10 hover:to-[hsl(var(--signer-blue))]/10',
+      fieldItemInitials:
+        'opacity-0 transition duration-200 group-hover/field-item:opacity-100 group-hover/field-item:bg-[hsl(var(--signer-blue))]',
+      comboxBoxItem:
+        'hover:bg-[hsl(var(--signer-blue)/15%)] active:bg-[hsl(var(--signer-blue)/15%)]',
+    },
+  },
+
+  purple: {
+    default: {
+      background: 'bg-[hsl(var(--signer-purple))]',
+      base: 'rounded-lg shadow-[0_0_0_5px_hsl(var(--signer-purple)/10%),0_0_0_2px_hsl(var(--signer-purple)/60%),0_0_0_0.5px_hsl(var(--signer-purple))]',
+      fieldItem:
+        'group/field-item p-2 border-none ring-none hover:bg-gradient-to-r hover:from-[hsl(var(--signer-purple))]/10 hover:to-[hsl(var(--signer-purple))]/10',
+      fieldItemInitials:
+        'opacity-0 transition duration-200 group-hover/field-item:opacity-100 group-hover/field-item:bg-[hsl(var(--signer-purple))]',
+      comboxBoxItem:
+        'hover:bg-[hsl(var(--signer-purple)/15%)] active:bg-[hsl(var(--signer-purple)/15%)]',
+    },
+  },
+
+  orange: {
+    default: {
+      background: 'bg-[hsl(var(--signer-orange))]',
+      base: 'rounded-lg shadow-[0_0_0_5px_hsl(var(--signer-orange)/10%),0_0_0_2px_hsl(var(--signer-orange)/60%),0_0_0_0.5px_hsl(var(--signer-orange))]',
+      fieldItem:
+        'group/field-item p-2 border-none ring-none hover:bg-gradient-to-r hover:from-[hsl(var(--signer-orange))]/10 hover:to-[hsl(var(--signer-orange))]/10',
+      fieldItemInitials:
+        'opacity-0 transition duration-200 group-hover/field-item:opacity-100 group-hover/field-item:bg-[hsl(var(--signer-orange))]',
+      comboxBoxItem:
+        'hover:bg-[hsl(var(--signer-orange)/15%)] active:bg-[hsl(var(--signer-orange)/15%)]',
+    },
+  },
+
+  yellow: {
+    default: {
+      background: 'bg-[hsl(var(--signer-yellow))]',
+      base: 'rounded-lg shadow-[0_0_0_5px_hsl(var(--signer-yellow)/10%),0_0_0_2px_hsl(var(--signer-yellow)/60%),0_0_0_0.5px_hsl(var(--signer-yellow))]',
+      fieldItem:
+        'group/field-item p-2 border-none ring-none hover:bg-gradient-to-r hover:from-[hsl(var(--signer-yellow))]/10 hover:to-[hsl(var(--signer-yellow))]/10',
+      fieldItemInitials:
+        'opacity-0 transition duration-200 group-hover/field-item:opacity-100 group-hover/field-item:bg-[hsl(var(--signer-yellow))]',
+      comboxBoxItem:
+        'hover:bg-[hsl(var(--signer-yellow)/15%)] active:bg-[hsl(var(--signer-yellow)/15%)]',
+    },
+  },
+
+  pink: {
+    default: {
+      background: 'bg-[hsl(var(--signer-pink))]',
+      base: 'rounded-lg shadow-[0_0_0_5px_hsl(var(--signer-pink)/10%),0_0_0_2px_hsl(var(--signer-pink)/60%),0_0_0_0.5px_hsl(var(--signer-pink))]',
+      fieldItem:
+        'group/field-item p-2 border-none ring-none hover:bg-gradient-to-r hover:from-[hsl(var(--signer-pink))]/10 hover:to-[hsl(var(--signer-pink))]/10',
+      fieldItemInitials:
+        'opacity-0 transition duration-200 group-hover/field-item:opacity-100 group-hover/field-item:bg-[hsl(var(--signer-pink))]',
+      comboxBoxItem:
+        'hover:bg-[hsl(var(--signer-pink)/15%)] active:bg-[hsl(var(--signer-pink)/15%)]',
+    },
+  },
+};
+
+export type CombinedStylesKey = keyof typeof SIGNER_COLOR_STYLES;
+
+export const AVAILABLE_SIGNER_COLORS = [
+  'green',
+  'blue',
+  'purple',
+  'orange',
+  'yellow',
+  'pink',
+] satisfies CombinedStylesKey[];
+
+export const useSignerColors = (index: number) => {
+  const key = AVAILABLE_SIGNER_COLORS[index % AVAILABLE_SIGNER_COLORS.length];
+
+  return SIGNER_COLOR_STYLES[key];
+};
+
+export const getSignerColorStyles = (index: number) => {
+  // Disabling the rule since the hook doesn't do anything special and can
+  // be used universally.
+  // eslint-disable-next-line react-hooks/rules-of-hooks
+  return useSignerColors(index);
+};
diff --git a/packages/ui/primitives/checkbox.tsx b/packages/ui/primitives/checkbox.tsx
index 18ff53d47..155f08df9 100644
--- a/packages/ui/primitives/checkbox.tsx
+++ b/packages/ui/primitives/checkbox.tsx
@@ -16,7 +16,7 @@ const Checkbox = React.forwardRef<
   <CheckboxPrimitive.Root
     ref={ref}
     className={cn(
-      'border-input bg-background ring-offset-background focus-visible:ring-ring data-[state=checked]:border-primary peer h-4 w-4 shrink-0 rounded-sm border focus-visible:outline-none focus-visible:ring-2 focus-visible:ring-offset-2 disabled:cursor-not-allowed disabled:opacity-50',
+      'border-input bg-background ring-offset-background focus-visible:ring-ring data-[state=checked]:border-primary data-[state=checked]:bg-primary peer h-4 w-4 shrink-0 rounded-sm border focus-visible:outline-none focus-visible:ring-2 focus-visible:ring-offset-2 disabled:cursor-not-allowed disabled:opacity-50',
       className,
     )}
     {...props}
diff --git a/packages/ui/primitives/document-flow/add-fields.tsx b/packages/ui/primitives/document-flow/add-fields.tsx
index bd0aee921..8fe8d66ed 100644
--- a/packages/ui/primitives/document-flow/add-fields.tsx
+++ b/packages/ui/primitives/document-flow/add-fields.tsx
@@ -4,18 +4,34 @@ import { useCallback, useEffect, useMemo, useRef, useState } from 'react';
 
 import { Caveat } from 'next/font/google';
 
-import { Check, ChevronsUpDown, Info } from 'lucide-react';
+import {
+  CalendarDays,
+  Check,
+  CheckSquare,
+  ChevronDown,
+  ChevronsUpDown,
+  Disc,
+  Hash,
+  Info,
+  Mail,
+  Type,
+  User,
+} from 'lucide-react';
 import { useFieldArray, useForm } from 'react-hook-form';
 
 import { getBoundingClientRect } from '@documenso/lib/client-only/get-bounding-client-rect';
 import { useDocumentElement } from '@documenso/lib/client-only/hooks/use-document-element';
 import { PDF_VIEWER_PAGE_SELECTOR } from '@documenso/lib/constants/pdf-viewer';
 import { RECIPIENT_ROLES_DESCRIPTION } from '@documenso/lib/constants/recipient-roles';
+import {
+  type TFieldMetaSchema as FieldMeta,
+  ZFieldMetaSchema,
+} from '@documenso/lib/types/field-meta';
 import { nanoid } from '@documenso/lib/universal/id';
 import type { Field, Recipient } from '@documenso/prisma/client';
-import { RecipientRole } from '@documenso/prisma/client';
-import { FieldType, SendStatus } from '@documenso/prisma/client';
+import { FieldType, RecipientRole, SendStatus } from '@documenso/prisma/client';
 
+import { getSignerColorStyles, useSignerColors } from '../../lib/signer-colors';
 import { cn } from '../../lib/utils';
 import { Button } from '../button';
 import { Card, CardContent } from '../card';
@@ -32,6 +48,7 @@ import {
   DocumentFlowFormContainerStep,
 } from './document-flow-root';
 import { FieldItem } from './field-item';
+import { FieldAdvancedSettings } from './field-item-advanced-settings';
 import { MissingSignatureFieldDialog } from './missing-signature-field-dialog';
 import { type DocumentFlowStep, FRIENDLY_FIELD_TYPE } from './types';
 
@@ -42,11 +59,21 @@ const fontCaveat = Caveat({
   variable: '--font-caveat',
 });
 
-const DEFAULT_HEIGHT_PERCENT = 5;
-const DEFAULT_WIDTH_PERCENT = 15;
+const MIN_HEIGHT_PX = 40;
+const MIN_WIDTH_PX = 140;
 
-const MIN_HEIGHT_PX = 60;
-const MIN_WIDTH_PX = 200;
+export type FieldFormType = {
+  nativeId?: number;
+  formId: string;
+  pageNumber: number;
+  type: FieldType;
+  pageX: number;
+  pageY: number;
+  pageWidth: number;
+  pageHeight: number;
+  signerEmail: string;
+  fieldMeta?: FieldMeta;
+};
 
 export type AddFieldsFormProps = {
   documentFlow: DocumentFlowStep;
@@ -56,8 +83,15 @@ export type AddFieldsFormProps = {
   onSubmit: (_data: TAddFieldsFormSchema) => void;
   canGoBack?: boolean;
   isDocumentPdfLoaded: boolean;
+  teamId?: number;
 };
 
+/*
+  I hate this, but due to TailwindCSS JIT, I couldnn't find a better way to do this for now.
+
+  TODO: Try to find a better way to do this.
+*/
+
 export const AddFieldsFormPartial = ({
   documentFlow,
   hideRecipients = false,
@@ -66,6 +100,7 @@ export const AddFieldsFormPartial = ({
   onSubmit,
   canGoBack = false,
   isDocumentPdfLoaded,
+  teamId,
 }: AddFieldsFormProps) => {
   const [isMissingSignatureDialogVisible, setIsMissingSignatureDialogVisible] = useState(false);
 
@@ -73,11 +108,15 @@ export const AddFieldsFormPartial = ({
   const { currentStep, totalSteps, previousStep } = useStep();
   const canRenderBackButtonAsRemove =
     currentStep === 1 && typeof documentFlow.onBackStep === 'function' && canGoBack;
+  const [showAdvancedSettings, setShowAdvancedSettings] = useState(false);
+  const [currentField, setCurrentField] = useState<FieldFormType>();
 
   const {
     control,
     handleSubmit,
     formState: { isSubmitting },
+    setValue,
+    getValues,
   } = useForm<TAddFieldsFormSchema>({
     defaultValues: {
       fields: fields.map((field) => ({
@@ -91,11 +130,30 @@ export const AddFieldsFormPartial = ({
         pageHeight: Number(field.height),
         signerEmail:
           recipients.find((recipient) => recipient.id === field.recipientId)?.email ?? '',
+        fieldMeta: field.fieldMeta ? ZFieldMetaSchema.parse(field.fieldMeta) : undefined,
       })),
     },
   });
 
   const onFormSubmit = handleSubmit(onSubmit);
+  const handleSavedFieldSettings = (fieldState: FieldMeta) => {
+    const initialValues = getValues();
+
+    const updatedFields = initialValues.fields.map((field) => {
+      if (field.formId === currentField?.formId) {
+        const parsedFieldMeta = ZFieldMetaSchema.parse(fieldState);
+
+        return {
+          ...field,
+          fieldMeta: parsedFieldMeta,
+        };
+      }
+
+      return field;
+    });
+
+    setValue('fields', updatedFields);
+  };
 
   const {
     append,
@@ -110,9 +168,45 @@ export const AddFieldsFormPartial = ({
   const [selectedField, setSelectedField] = useState<FieldType | null>(null);
   const [selectedSigner, setSelectedSigner] = useState<Recipient | null>(null);
   const [showRecipientsSelector, setShowRecipientsSelector] = useState(false);
+  const selectedSignerIndex = recipients.findIndex((r) => r.id === selectedSigner?.id);
+  const selectedSignerStyles = useSignerColors(
+    selectedSignerIndex === -1 ? 0 : selectedSignerIndex,
+  );
 
   const hasSelectedSignerBeenSent = selectedSigner?.sendStatus === SendStatus.SENT;
 
+  const filterFieldsWithEmptyValues = (fields: typeof localFields, fieldType: string) =>
+    fields
+      .filter((field) => field.type === fieldType)
+      .filter((field) => {
+        if (field.fieldMeta && 'values' in field.fieldMeta) {
+          return field.fieldMeta.values?.length === 0;
+        }
+
+        return true;
+      });
+
+  const emptyCheckboxFields = useMemo(
+    () => filterFieldsWithEmptyValues(localFields, FieldType.CHECKBOX),
+    // eslint-disable-next-line react-hooks/exhaustive-deps
+    [localFields],
+  );
+
+  const emptyRadioFields = useMemo(
+    () => filterFieldsWithEmptyValues(localFields, FieldType.RADIO),
+    // eslint-disable-next-line react-hooks/exhaustive-deps
+    [localFields],
+  );
+
+  const emptySelectFields = useMemo(
+    () => filterFieldsWithEmptyValues(localFields, FieldType.DROPDOWN),
+    // eslint-disable-next-line react-hooks/exhaustive-deps
+    [localFields],
+  );
+
+  const hasErrors =
+    emptyCheckboxFields.length > 0 || emptyRadioFields.length > 0 || emptySelectFields.length > 0;
+
   const isFieldsDisabled =
     !selectedSigner ||
     hasSelectedSignerBeenSent ||
@@ -195,6 +289,7 @@ export const AddFieldsFormPartial = ({
         pageWidth: fieldPageWidth,
         pageHeight: fieldPageHeight,
         signerEmail: selectedSigner.email,
+        fieldMeta: undefined,
       });
 
       setIsFieldWithinBounds(false);
@@ -276,11 +371,9 @@ export const AddFieldsFormPartial = ({
         return;
       }
 
-      const { height, width } = $page.getBoundingClientRect();
-
       fieldBounds.current = {
-        height: Math.max(height * (DEFAULT_HEIGHT_PERCENT / 100), MIN_HEIGHT_PX),
-        width: Math.max(width * (DEFAULT_WIDTH_PERCENT / 100), MIN_WIDTH_PX),
+        height: Math.max(MIN_HEIGHT_PX),
+        width: Math.max(MIN_WIDTH_PX),
       };
     });
 
@@ -320,6 +413,10 @@ export const AddFieldsFormPartial = ({
     );
   }, [recipientsByRole]);
 
+  const handleAdvancedSettings = () => {
+    setShowAdvancedSettings((prev) => !prev);
+  };
+
   const handleGoNextClick = () => {
     const everySignerHasSignature = recipientsByRole.SIGNER.every((signer) =>
       localFields.some(
@@ -338,297 +435,473 @@ export const AddFieldsFormPartial = ({
 
   return (
     <>
-      <DocumentFlowFormContainerHeader
-        title={documentFlow.title}
-        description={documentFlow.description}
-      />
-
-      <DocumentFlowFormContainerContent>
-        <div className="flex flex-col">
-          {selectedField && (
-            <Card
-              className={cn(
-                'bg-field-card/80 pointer-events-none fixed z-50 cursor-pointer border-2 backdrop-blur-[1px]',
-                {
-                  'border-field-card-border': isFieldWithinBounds,
-                  'opacity-50': !isFieldWithinBounds,
-                },
-              )}
-              style={{
-                top: coords.y,
-                left: coords.x,
-                height: fieldBounds.current.height,
-                width: fieldBounds.current.width,
-              }}
-            >
-              <CardContent className="text-field-card-foreground flex h-full w-full items-center justify-center p-2">
-                {FRIENDLY_FIELD_TYPE[selectedField]}
-              </CardContent>
-            </Card>
-          )}
-
-          {isDocumentPdfLoaded &&
-            localFields.map((field, index) => (
-              <FieldItem
-                key={index}
-                field={field}
-                disabled={selectedSigner?.email !== field.signerEmail || hasSelectedSignerBeenSent}
-                minHeight={fieldBounds.current.height}
-                minWidth={fieldBounds.current.width}
-                passive={isFieldWithinBounds && !!selectedField}
-                onResize={(options) => onFieldResize(options, index)}
-                onMove={(options) => onFieldMove(options, index)}
-                onRemove={() => remove(index)}
-              />
-            ))}
-
-          {!hideRecipients && (
-            <Popover open={showRecipientsSelector} onOpenChange={setShowRecipientsSelector}>
-              <PopoverTrigger asChild>
-                <Button
-                  type="button"
-                  variant="outline"
-                  role="combobox"
-                  className="bg-background text-muted-foreground mb-12 justify-between font-normal"
+      {showAdvancedSettings && currentField ? (
+        <FieldAdvancedSettings
+          title="Advanced settings"
+          description={`Configure the ${FRIENDLY_FIELD_TYPE[currentField.type]} field`}
+          field={currentField}
+          fields={localFields}
+          onAdvancedSettings={handleAdvancedSettings}
+          isDocumentPdfLoaded={isDocumentPdfLoaded}
+          onSave={handleSavedFieldSettings}
+          teamId={teamId}
+        />
+      ) : (
+        <>
+          <DocumentFlowFormContainerHeader
+            title={documentFlow.title}
+            description={documentFlow.description}
+          />
+          <DocumentFlowFormContainerContent>
+            <div className="flex flex-col">
+              {selectedField && (
+                <div
+                  className={cn(
+                    'pointer-events-none fixed z-50 flex cursor-pointer flex-col items-center justify-center bg-white transition duration-200',
+                    selectedSignerStyles.default.base,
+                    {
+                      '-rotate-6 scale-90 opacity-50': !isFieldWithinBounds,
+                    },
+                  )}
+                  style={{
+                    top: coords.y,
+                    left: coords.x,
+                    height: fieldBounds.current.height,
+                    width: fieldBounds.current.width,
+                  }}
                 >
-                  {selectedSigner?.email && (
-                    <span className="flex-1 truncate text-left">
-                      {selectedSigner?.name} ({selectedSigner?.email})
-                    </span>
-                  )}
+                  {FRIENDLY_FIELD_TYPE[selectedField]}
+                </div>
+              )}
 
-                  {!selectedSigner?.email && (
-                    <span className="flex-1 truncate text-left">{selectedSigner?.email}</span>
-                  )}
+              {isDocumentPdfLoaded &&
+                localFields.map((field, index) => {
+                  const recipientIndex = recipients.findIndex((r) => r.email === field.signerEmail);
 
-                  <ChevronsUpDown className="ml-2 h-4 w-4" />
-                </Button>
-              </PopoverTrigger>
+                  return (
+                    <FieldItem
+                      key={index}
+                      recipientIndex={recipientIndex === -1 ? 0 : recipientIndex}
+                      field={field}
+                      disabled={
+                        selectedSigner?.email !== field.signerEmail || hasSelectedSignerBeenSent
+                      }
+                      minHeight={fieldBounds.current.height}
+                      minWidth={fieldBounds.current.width}
+                      passive={isFieldWithinBounds && !!selectedField}
+                      onResize={(options) => onFieldResize(options, index)}
+                      onMove={(options) => onFieldMove(options, index)}
+                      onRemove={() => remove(index)}
+                      onAdvancedSettings={() => {
+                        setCurrentField(field);
+                        handleAdvancedSettings();
+                      }}
+                      hideRecipients={hideRecipients}
+                    />
+                  );
+                })}
 
-              <PopoverContent className="p-0" align="start">
-                <Command value={selectedSigner?.email}>
-                  <CommandInput />
-
-                  <CommandEmpty>
-                    <span className="text-muted-foreground inline-block px-4">
-                      No recipient matching this description was found.
-                    </span>
-                  </CommandEmpty>
-
-                  {recipientsByRoleToDisplay.map(([role, recipients], roleIndex) => (
-                    <CommandGroup key={roleIndex}>
-                      <div className="text-muted-foreground mb-1 ml-2 mt-2 text-xs font-medium">
-                        {`${RECIPIENT_ROLES_DESCRIPTION[role].roleName}s`}
-                      </div>
-
-                      {recipients.length === 0 && (
-                        <div
-                          key={`${role}-empty`}
-                          className="text-muted-foreground/80 px-4 pb-4 pt-2.5 text-center text-xs"
-                        >
-                          No recipients with this role
-                        </div>
+              {!hideRecipients && (
+                <Popover open={showRecipientsSelector} onOpenChange={setShowRecipientsSelector}>
+                  <PopoverTrigger asChild>
+                    <Button
+                      type="button"
+                      variant="outline"
+                      role="combobox"
+                      className={cn(
+                        'bg-background text-muted-foreground hover:text-foreground mb-12 mt-2 justify-between font-normal',
+                        selectedSignerStyles.default.base,
+                      )}
+                    >
+                      {selectedSigner?.email && (
+                        <span className="flex-1 truncate text-left">
+                          {selectedSigner?.name} ({selectedSigner?.email})
+                        </span>
                       )}
 
-                      {recipients.map((recipient) => (
-                        <CommandItem
-                          key={recipient.id}
-                          className={cn('px-2 last:mb-1 [&:not(:first-child)]:mt-1', {
-                            'text-muted-foreground': recipient.sendStatus === SendStatus.SENT,
-                          })}
-                          onSelect={() => {
-                            setSelectedSigner(recipient);
-                            setShowRecipientsSelector(false);
-                          }}
-                        >
-                          <span
-                            className={cn('text-foreground/70 truncate', {
-                              'text-foreground/80': recipient === selectedSigner,
-                            })}
-                          >
-                            {recipient.name && (
-                              <span title={`${recipient.name} (${recipient.email})`}>
-                                {recipient.name} ({recipient.email})
-                              </span>
-                            )}
+                      {!selectedSigner?.email && (
+                        <span className="gradie flex-1 truncate text-left">
+                          {selectedSigner?.email}
+                        </span>
+                      )}
 
-                            {!recipient.name && (
-                              <span title={recipient.email}>{recipient.email}</span>
-                            )}
-                          </span>
+                      <ChevronsUpDown className="ml-2 h-4 w-4" />
+                    </Button>
+                  </PopoverTrigger>
 
-                          <div className="ml-auto flex items-center justify-center">
-                            {recipient.sendStatus !== SendStatus.SENT ? (
-                              <Check
-                                aria-hidden={recipient !== selectedSigner}
-                                className={cn('h-4 w-4 flex-shrink-0', {
-                                  'opacity-0': recipient !== selectedSigner,
-                                  'opacity-100': recipient === selectedSigner,
-                                })}
-                              />
-                            ) : (
-                              <Tooltip>
-                                <TooltipTrigger>
-                                  <Info className="ml-2 h-4 w-4" />
-                                </TooltipTrigger>
+                  <PopoverContent className="p-0" align="start">
+                    <Command value={selectedSigner?.email}>
+                      <CommandInput />
 
-                                <TooltipContent className="text-muted-foreground max-w-xs">
-                                  This document has already been sent to this recipient. You can no
-                                  longer edit this recipient.
-                                </TooltipContent>
-                              </Tooltip>
-                            )}
+                      <CommandEmpty>
+                        <span className="text-muted-foreground inline-block px-4">
+                          No recipient matching this description was found.
+                        </span>
+                      </CommandEmpty>
+
+                      {recipientsByRoleToDisplay.map(([role, roleRecipients], roleIndex) => (
+                        <CommandGroup key={roleIndex}>
+                          <div className="text-muted-foreground mb-1 ml-2 mt-2 text-xs font-medium">
+                            {`${RECIPIENT_ROLES_DESCRIPTION[role].roleName}s`}
                           </div>
-                        </CommandItem>
+
+                          {roleRecipients.length === 0 && (
+                            <div
+                              key={`${role}-empty`}
+                              className="text-muted-foreground/80 px-4 pb-4 pt-2.5 text-center text-xs"
+                            >
+                              No recipients with this role
+                            </div>
+                          )}
+
+                          {roleRecipients.map((recipient) => (
+                            <CommandItem
+                              key={recipient.id}
+                              className={cn(
+                                'px-2 last:mb-1 [&:not(:first-child)]:mt-1',
+                                getSignerColorStyles(
+                                  Math.max(
+                                    recipients.findIndex((r) => r.id === recipient.id),
+                                    0,
+                                  ),
+                                ).default.comboxBoxItem,
+                                {
+                                  'text-muted-foreground': recipient.sendStatus === SendStatus.SENT,
+                                },
+                              )}
+                              onSelect={() => {
+                                setSelectedSigner(recipient);
+                                setShowRecipientsSelector(false);
+                              }}
+                            >
+                              <span
+                                className={cn('text-foreground/70 truncate', {
+                                  'text-foreground/80': recipient === selectedSigner,
+                                })}
+                              >
+                                {recipient.name && (
+                                  <span title={`${recipient.name} (${recipient.email})`}>
+                                    {recipient.name} ({recipient.email})
+                                  </span>
+                                )}
+
+                                {!recipient.name && (
+                                  <span title={recipient.email}>{recipient.email}</span>
+                                )}
+                              </span>
+
+                              <div className="ml-auto flex items-center justify-center">
+                                {recipient.sendStatus !== SendStatus.SENT ? (
+                                  <Check
+                                    aria-hidden={recipient !== selectedSigner}
+                                    className={cn('h-4 w-4 flex-shrink-0', {
+                                      'opacity-0': recipient !== selectedSigner,
+                                      'opacity-100': recipient === selectedSigner,
+                                    })}
+                                  />
+                                ) : (
+                                  <Tooltip>
+                                    <TooltipTrigger>
+                                      <Info className="ml-2 h-4 w-4" />
+                                    </TooltipTrigger>
+
+                                    <TooltipContent className="text-muted-foreground max-w-xs">
+                                      This document has already been sent to this recipient. You can
+                                      no longer edit this recipient.
+                                    </TooltipContent>
+                                  </Tooltip>
+                                )}
+                              </div>
+                            </CommandItem>
+                          ))}
+                        </CommandGroup>
                       ))}
-                    </CommandGroup>
-                  ))}
-                </Command>
-              </PopoverContent>
-            </Popover>
+                    </Command>
+                  </PopoverContent>
+                </Popover>
+              )}
+
+              <div className="-mx-2 flex-1 overflow-y-auto px-2">
+                <fieldset disabled={isFieldsDisabled} className="my-2 grid grid-cols-3 gap-4">
+                  <button
+                    type="button"
+                    className="group h-full w-full"
+                    onClick={() => setSelectedField(FieldType.SIGNATURE)}
+                    onMouseDown={() => setSelectedField(FieldType.SIGNATURE)}
+                    data-selected={selectedField === FieldType.SIGNATURE ? true : undefined}
+                  >
+                    <Card
+                      className={cn(
+                        'flex h-full w-full cursor-pointer items-center justify-center group-disabled:opacity-50',
+                        // selectedSignerStyles.borderClass,
+                      )}
+                    >
+                      <CardContent className="flex flex-col items-center justify-center px-6 py-4">
+                        <p
+                          className={cn(
+                            'text-muted-foreground group-data-[selected]:text-foreground flex items-center justify-center gap-x-1.5 text-lg font-normal',
+                            fontCaveat.className,
+                          )}
+                        >
+                          Signature
+                        </p>
+                      </CardContent>
+                    </Card>
+                  </button>
+
+                  <button
+                    type="button"
+                    className="group h-full w-full"
+                    onClick={() => setSelectedField(FieldType.EMAIL)}
+                    onMouseDown={() => setSelectedField(FieldType.EMAIL)}
+                    data-selected={selectedField === FieldType.EMAIL ? true : undefined}
+                  >
+                    <Card
+                      className={cn(
+                        'flex h-full w-full cursor-pointer items-center justify-center group-disabled:opacity-50',
+                        // selectedSignerStyles.borderClass,
+                      )}
+                    >
+                      <CardContent className="p-4">
+                        <p
+                          className={cn(
+                            'text-muted-foreground group-data-[selected]:text-foreground flex items-center justify-center gap-x-1.5 text-sm font-normal',
+                          )}
+                        >
+                          <Mail className="h-4 w-4" />
+                          Email
+                        </p>
+                      </CardContent>
+                    </Card>
+                  </button>
+
+                  <button
+                    type="button"
+                    className="group h-full w-full"
+                    onClick={() => setSelectedField(FieldType.NAME)}
+                    onMouseDown={() => setSelectedField(FieldType.NAME)}
+                    data-selected={selectedField === FieldType.NAME ? true : undefined}
+                  >
+                    <Card
+                      className={cn(
+                        'flex h-full w-full cursor-pointer items-center justify-center group-disabled:opacity-50',
+                        // selectedSignerStyles.borderClass,
+                      )}
+                    >
+                      <CardContent className="p-4">
+                        <p
+                          className={cn(
+                            'text-muted-foreground group-data-[selected]:text-foreground flex items-center justify-center gap-x-1.5 text-sm font-normal',
+                          )}
+                        >
+                          <User className="h-4 w-4" />
+                          Name
+                        </p>
+                      </CardContent>
+                    </Card>
+                  </button>
+
+                  <button
+                    type="button"
+                    className="group h-full w-full"
+                    onClick={() => setSelectedField(FieldType.DATE)}
+                    onMouseDown={() => setSelectedField(FieldType.DATE)}
+                    data-selected={selectedField === FieldType.DATE ? true : undefined}
+                  >
+                    <Card
+                      className={cn(
+                        'flex h-full w-full cursor-pointer items-center justify-center group-disabled:opacity-50',
+                        // selectedSignerStyles.borderClass,
+                      )}
+                    >
+                      <CardContent className="p-4">
+                        <p
+                          className={cn(
+                            'text-muted-foreground group-data-[selected]:text-foreground flex items-center justify-center gap-x-1.5 text-sm font-normal',
+                          )}
+                        >
+                          <CalendarDays className="h-4 w-4" />
+                          Date
+                        </p>
+                      </CardContent>
+                    </Card>
+                  </button>
+
+                  <button
+                    type="button"
+                    className="group h-full w-full"
+                    onClick={() => setSelectedField(FieldType.TEXT)}
+                    onMouseDown={() => setSelectedField(FieldType.TEXT)}
+                    data-selected={selectedField === FieldType.TEXT ? true : undefined}
+                  >
+                    <Card
+                      className={cn(
+                        'flex h-full w-full cursor-pointer items-center justify-center group-disabled:opacity-50',
+                        // selectedSignerStyles.borderClass,
+                      )}
+                    >
+                      <CardContent className="p-4">
+                        <p
+                          className={cn(
+                            'text-muted-foreground group-data-[selected]:text-foreground flex items-center justify-center gap-x-1.5 text-sm font-normal',
+                          )}
+                        >
+                          <Type className="h-4 w-4" />
+                          Text
+                        </p>
+                      </CardContent>
+                    </Card>
+                  </button>
+
+                  <button
+                    type="button"
+                    className="group h-full w-full"
+                    onClick={() => setSelectedField(FieldType.NUMBER)}
+                    onMouseDown={() => setSelectedField(FieldType.NUMBER)}
+                    data-selected={selectedField === FieldType.NUMBER ? true : undefined}
+                  >
+                    <Card
+                      className={cn(
+                        'flex h-full w-full cursor-pointer items-center justify-center group-disabled:opacity-50',
+                        // selectedSignerStyles.borderClass,
+                      )}
+                    >
+                      <CardContent className="p-4">
+                        <p
+                          className={cn(
+                            'text-muted-foreground group-data-[selected]:text-foreground flex items-center justify-center gap-x-1.5 text-sm font-normal',
+                          )}
+                        >
+                          <Hash className="h-4 w-4" />
+                          Number
+                        </p>
+                      </CardContent>
+                    </Card>
+                  </button>
+
+                  <button
+                    type="button"
+                    className="group h-full w-full"
+                    onClick={() => setSelectedField(FieldType.RADIO)}
+                    onMouseDown={() => setSelectedField(FieldType.RADIO)}
+                    data-selected={selectedField === FieldType.RADIO ? true : undefined}
+                  >
+                    <Card
+                      className={cn(
+                        'flex h-full w-full cursor-pointer items-center justify-center group-disabled:opacity-50',
+                        // selectedSignerStyles.borderClass,
+                      )}
+                    >
+                      <CardContent className="p-4">
+                        <p
+                          className={cn(
+                            'text-muted-foreground group-data-[selected]:text-foreground flex items-center justify-center gap-x-1.5 text-sm font-normal',
+                          )}
+                        >
+                          <Disc className="h-4 w-4" />
+                          Radio
+                        </p>
+                      </CardContent>
+                    </Card>
+                  </button>
+
+                  <button
+                    type="button"
+                    className="group h-full w-full"
+                    onClick={() => setSelectedField(FieldType.CHECKBOX)}
+                    onMouseDown={() => setSelectedField(FieldType.CHECKBOX)}
+                    data-selected={selectedField === FieldType.CHECKBOX ? true : undefined}
+                  >
+                    <Card
+                      className={cn(
+                        'flex h-full w-full cursor-pointer items-center justify-center group-disabled:opacity-50',
+                        // selectedSignerStyles.borderClass,
+                      )}
+                    >
+                      <CardContent className="p-4">
+                        <p
+                          className={cn(
+                            'text-muted-foreground group-data-[selected]:text-foreground flex items-center justify-center gap-x-1.5 text-sm font-normal',
+                          )}
+                        >
+                          <CheckSquare className="h-4 w-4" />
+                          Checkbox
+                        </p>
+                      </CardContent>
+                    </Card>
+                  </button>
+
+                  <button
+                    type="button"
+                    className="group h-full w-full"
+                    onClick={() => setSelectedField(FieldType.DROPDOWN)}
+                    onMouseDown={() => setSelectedField(FieldType.DROPDOWN)}
+                    data-selected={selectedField === FieldType.DROPDOWN ? true : undefined}
+                  >
+                    <Card
+                      className={cn(
+                        'flex h-full w-full cursor-pointer items-center justify-center group-disabled:opacity-50',
+                        // selectedSignerStyles.borderClass,
+                      )}
+                    >
+                      <CardContent className="p-4">
+                        <p
+                          className={cn(
+                            'text-muted-foreground group-data-[selected]:text-foreground flex items-center justify-center gap-x-1.5 text-sm font-normal',
+                          )}
+                        >
+                          <ChevronDown className="h-4 w-4" />
+                          Dropdown
+                        </p>
+                      </CardContent>
+                    </Card>
+                  </button>
+                </fieldset>
+              </div>
+            </div>
+          </DocumentFlowFormContainerContent>
+          {hasErrors && (
+            <div className="mt-4">
+              <ul>
+                <li className="text-sm text-red-500">
+                  To proceed further, please set at least one value for the{' '}
+                  {emptyCheckboxFields.length > 0
+                    ? 'Checkbox'
+                    : emptyRadioFields.length > 0
+                    ? 'Radio'
+                    : 'Select'}{' '}
+                  field.
+                </li>
+              </ul>
+            </div>
           )}
+          <DocumentFlowFormContainerFooter>
+            <DocumentFlowFormContainerStep
+              title={documentFlow.title}
+              step={currentStep}
+              maxStep={totalSteps}
+            />
 
-          <div className="-mx-2 flex-1 overflow-y-auto px-2">
-            <fieldset disabled={isFieldsDisabled} className="grid grid-cols-2 gap-x-4 gap-y-8">
-              <button
-                type="button"
-                className="group h-full w-full"
-                onClick={() => setSelectedField(FieldType.SIGNATURE)}
-                onMouseDown={() => setSelectedField(FieldType.SIGNATURE)}
-                data-selected={selectedField === FieldType.SIGNATURE ? true : undefined}
-              >
-                <Card className="group-data-[selected]:border-documenso h-full w-full cursor-pointer group-disabled:opacity-50">
-                  <CardContent className="flex flex-col items-center justify-center px-6 py-4">
-                    <p
-                      className={cn(
-                        'text-muted-foreground group-data-[selected]:text-foreground w-full truncate text-3xl font-medium',
-                        fontCaveat.className,
-                      )}
-                    >
-                      {selectedSigner?.name || 'Signature'}
-                    </p>
+            <DocumentFlowFormContainerActions
+              loading={isSubmitting}
+              disabled={isSubmitting}
+              disableNextStep={hasErrors}
+              onGoBackClick={() => {
+                previousStep();
+                remove();
+                documentFlow.onBackStep?.();
+              }}
+              goBackLabel={canRenderBackButtonAsRemove ? 'Remove' : undefined}
+              onGoNextClick={handleGoNextClick}
+            />
+          </DocumentFlowFormContainerFooter>
 
-                    <p className="text-muted-foreground mt-2 text-center text-xs">Signature</p>
-                  </CardContent>
-                </Card>
-              </button>
-
-              <button
-                type="button"
-                className="group h-full w-full"
-                onClick={() => setSelectedField(FieldType.EMAIL)}
-                onMouseDown={() => setSelectedField(FieldType.EMAIL)}
-                data-selected={selectedField === FieldType.EMAIL ? true : undefined}
-              >
-                <Card className="group-data-[selected]:border-documenso h-full w-full cursor-pointer group-disabled:opacity-50">
-                  <CardContent className="flex flex-col items-center justify-center px-6 py-4">
-                    <p
-                      className={cn(
-                        'text-muted-foreground group-data-[selected]:text-foreground text-xl font-medium',
-                      )}
-                    >
-                      {'Email'}
-                    </p>
-
-                    <p className="text-muted-foreground mt-2 text-xs">Email</p>
-                  </CardContent>
-                </Card>
-              </button>
-
-              <button
-                type="button"
-                className="group h-full w-full"
-                onClick={() => setSelectedField(FieldType.NAME)}
-                onMouseDown={() => setSelectedField(FieldType.NAME)}
-                data-selected={selectedField === FieldType.NAME ? true : undefined}
-              >
-                <Card className="group-data-[selected]:border-documenso h-full w-full cursor-pointer group-disabled:opacity-50">
-                  <CardContent className="flex flex-col items-center justify-center px-6 py-4">
-                    <p
-                      className={cn(
-                        'text-muted-foreground group-data-[selected]:text-foreground text-xl font-medium',
-                      )}
-                    >
-                      {'Name'}
-                    </p>
-
-                    <p className="text-muted-foreground mt-2 text-xs">Name</p>
-                  </CardContent>
-                </Card>
-              </button>
-
-              <button
-                type="button"
-                className="group h-full w-full"
-                onClick={() => setSelectedField(FieldType.DATE)}
-                onMouseDown={() => setSelectedField(FieldType.DATE)}
-                data-selected={selectedField === FieldType.DATE ? true : undefined}
-              >
-                <Card className="group-data-[selected]:border-documenso h-full w-full cursor-pointer group-disabled:opacity-50">
-                  <CardContent className="flex flex-col items-center justify-center px-6 py-4">
-                    <p
-                      className={cn(
-                        'text-muted-foreground group-data-[selected]:text-foreground text-xl font-medium',
-                      )}
-                    >
-                      {'Date'}
-                    </p>
-
-                    <p className="text-muted-foreground mt-2 text-xs">Date</p>
-                  </CardContent>
-                </Card>
-              </button>
-
-              <button
-                type="button"
-                className="group h-full w-full"
-                onClick={() => setSelectedField(FieldType.TEXT)}
-                onMouseDown={() => setSelectedField(FieldType.TEXT)}
-                data-selected={selectedField === FieldType.TEXT ? true : undefined}
-              >
-                <Card className="group-data-[selected]:border-documenso h-full w-full cursor-pointer group-disabled:opacity-50">
-                  <CardContent className="flex flex-col items-center justify-center px-6 py-4">
-                    <p
-                      className={cn(
-                        'text-muted-foreground group-data-[selected]:text-foreground text-xl font-medium',
-                      )}
-                    >
-                      {'Text'}
-                    </p>
-
-                    <p className="text-muted-foreground mt-2 text-xs">Custom Text</p>
-                  </CardContent>
-                </Card>
-              </button>
-            </fieldset>
-          </div>
-        </div>
-      </DocumentFlowFormContainerContent>
-
-      <DocumentFlowFormContainerFooter>
-        <DocumentFlowFormContainerStep
-          title={documentFlow.title}
-          step={currentStep}
-          maxStep={totalSteps}
-        />
-
-        <DocumentFlowFormContainerActions
-          loading={isSubmitting}
-          disabled={isSubmitting}
-          onGoBackClick={() => {
-            previousStep();
-            remove();
-            documentFlow.onBackStep?.();
-          }}
-          goBackLabel={canRenderBackButtonAsRemove ? 'Remove' : undefined}
-          onGoNextClick={handleGoNextClick}
-        />
-      </DocumentFlowFormContainerFooter>
-
-      <MissingSignatureFieldDialog
-        isOpen={isMissingSignatureDialogVisible}
-        onOpenChange={(value) => setIsMissingSignatureDialogVisible(value)}
-      />
+          <MissingSignatureFieldDialog
+            isOpen={isMissingSignatureDialogVisible}
+            onOpenChange={(value) => setIsMissingSignatureDialogVisible(value)}
+          />
+        </>
+      )}
     </>
   );
 };
diff --git a/packages/ui/primitives/document-flow/add-fields.types.ts b/packages/ui/primitives/document-flow/add-fields.types.ts
index e7a509632..7309250a8 100644
--- a/packages/ui/primitives/document-flow/add-fields.types.ts
+++ b/packages/ui/primitives/document-flow/add-fields.types.ts
@@ -1,5 +1,6 @@
 import { z } from 'zod';
 
+import { ZFieldMetaSchema } from '@documenso/lib/types/field-meta';
 import { FieldType } from '@documenso/prisma/client';
 
 export const ZAddFieldsFormSchema = z.object({
@@ -14,6 +15,7 @@ export const ZAddFieldsFormSchema = z.object({
       pageY: z.number().min(0),
       pageWidth: z.number().min(0),
       pageHeight: z.number().min(0),
+      fieldMeta: ZFieldMetaSchema,
     }),
   ),
 });
diff --git a/packages/ui/primitives/document-flow/add-signature.tsx b/packages/ui/primitives/document-flow/add-signature.tsx
index f1ebc885e..38348ec0d 100644
--- a/packages/ui/primitives/document-flow/add-signature.tsx
+++ b/packages/ui/primitives/document-flow/add-signature.tsx
@@ -59,7 +59,6 @@ export const AddSignatureFormPartial = ({
   requireSignature = true,
 }: AddSignatureFormProps) => {
   const { currentStep, totalSteps } = useStep();
-
   const [validateUninsertedFields, setValidateUninsertedFields] = useState(false);
 
   // Refined schema which takes into account whether to allow an empty name or signature.
@@ -147,6 +146,26 @@ export const AddSignatureFormPartial = ({
       return !form.formState.errors.customText;
     }
 
+    if (fieldType === FieldType.NUMBER) {
+      await form.trigger('number');
+      return !form.formState.errors.number;
+    }
+
+    if (fieldType === FieldType.RADIO) {
+      await form.trigger('radio');
+      return !form.formState.errors.radio;
+    }
+
+    if (fieldType === FieldType.CHECKBOX) {
+      await form.trigger('checkbox');
+      return !form.formState.errors.checkbox;
+    }
+
+    if (fieldType === FieldType.DROPDOWN) {
+      await form.trigger('dropdown');
+      return !form.formState.errors.dropdown;
+    }
+
     return true;
   };
 
@@ -170,7 +189,7 @@ export const AddSignatureFormPartial = ({
         customText: form.getValues('name'),
         inserted: true,
       }))
-      .with(FieldType.TEXT, () => ({
+      .with(FieldType.TEXT, FieldType.NUMBER, FieldType.RADIO, FieldType.CHECKBOX, () => ({
         ...field,
         customText: form.getValues('customText'),
         inserted: true,
@@ -374,15 +393,25 @@ export const AddSignatureFormPartial = ({
         <ElementVisible target={PDF_VIEWER_PAGE_SELECTOR}>
           {localFields.map((field) =>
             match(field.type)
-              .with(FieldType.DATE, FieldType.TEXT, FieldType.EMAIL, FieldType.NAME, () => {
-                return (
-                  <SinglePlayerModeCustomTextField
-                    onClick={insertField(field)}
-                    key={field.id}
-                    field={field}
-                  />
-                );
-              })
+              .with(
+                FieldType.DATE,
+                FieldType.TEXT,
+                FieldType.EMAIL,
+                FieldType.NAME,
+                FieldType.NUMBER,
+                FieldType.CHECKBOX,
+                FieldType.RADIO,
+                FieldType.DROPDOWN,
+                () => {
+                  return (
+                    <SinglePlayerModeCustomTextField
+                      onClick={insertField(field)}
+                      key={field.id}
+                      field={field}
+                    />
+                  );
+                },
+              )
               .with(FieldType.SIGNATURE, () => (
                 <SinglePlayerModeSignatureField
                   onClick={insertField(field)}
diff --git a/packages/ui/primitives/document-flow/add-signature.types.ts b/packages/ui/primitives/document-flow/add-signature.types.ts
index 380091acf..29c505a66 100644
--- a/packages/ui/primitives/document-flow/add-signature.types.ts
+++ b/packages/ui/primitives/document-flow/add-signature.types.ts
@@ -7,6 +7,10 @@ export const ZAddSignatureFormSchema = z.object({
     .email({ message: 'Invalid email address' }),
   name: z.string(),
   customText: z.string(),
+  number: z.number().optional(),
+  radio: z.string().optional(),
+  checkbox: z.boolean().optional(),
+  dropdown: z.string().optional(),
   signature: z.string(),
 });
 
diff --git a/packages/ui/primitives/document-flow/advanced-fields/checkbox.tsx b/packages/ui/primitives/document-flow/advanced-fields/checkbox.tsx
new file mode 100644
index 000000000..695cd1821
--- /dev/null
+++ b/packages/ui/primitives/document-flow/advanced-fields/checkbox.tsx
@@ -0,0 +1,47 @@
+import { ZCheckboxFieldMeta } from '@documenso/lib/types/field-meta';
+import type { TCheckboxFieldMeta } from '@documenso/lib/types/field-meta';
+import { Checkbox } from '@documenso/ui/primitives/checkbox';
+import { Label } from '@documenso/ui/primitives/label';
+
+import { FieldIcon } from '../field-icon';
+import type { TDocumentFlowFormSchema } from '../types';
+
+type Field = TDocumentFlowFormSchema['fields'][0];
+
+export type CheckboxFieldProps = {
+  field: Field;
+};
+
+export const CheckboxField = ({ field }: CheckboxFieldProps) => {
+  let parsedFieldMeta: TCheckboxFieldMeta | undefined = undefined;
+
+  if (field.fieldMeta) {
+    parsedFieldMeta = ZCheckboxFieldMeta.parse(field.fieldMeta);
+  }
+
+  if (parsedFieldMeta && (!parsedFieldMeta.values || parsedFieldMeta.values.length === 0)) {
+    return (
+      <FieldIcon fieldMeta={field.fieldMeta} type={field.type} signerEmail={field.signerEmail} />
+    );
+  }
+
+  return (
+    <div className='flex flex-col gap-y-2'>
+      {!parsedFieldMeta?.values ? (
+        <FieldIcon fieldMeta={field.fieldMeta} type={field.type} signerEmail={field.signerEmail} />
+      ) : (
+        parsedFieldMeta.values.map((item: { value: string; checked: boolean }, index: number) => (
+          <div key={index} className='flex items-center gap-x-1.5'>
+            <Checkbox
+              className="h-4 w-4"
+              checkClassName="text-white"
+              id={`checkbox-${index}`}
+              checked={item.checked}
+            />
+            <Label htmlFor={`checkbox-${index}`}>{item.value}</Label>
+          </div>
+        ))
+      )}
+    </div>
+  );
+};
diff --git a/packages/ui/primitives/document-flow/advanced-fields/radio.tsx b/packages/ui/primitives/document-flow/advanced-fields/radio.tsx
new file mode 100644
index 000000000..5e98fb424
--- /dev/null
+++ b/packages/ui/primitives/document-flow/advanced-fields/radio.tsx
@@ -0,0 +1,49 @@
+import { ZRadioFieldMeta } from '@documenso/lib/types/field-meta';
+import type { TRadioFieldMeta } from '@documenso/lib/types/field-meta';
+import { Label } from '@documenso/ui/primitives/label';
+import { RadioGroup, RadioGroupItem } from '@documenso/ui/primitives/radio-group';
+
+import { FieldIcon } from '../field-icon';
+import type { TDocumentFlowFormSchema } from '../types';
+
+type Field = TDocumentFlowFormSchema['fields'][0];
+
+export type RadioFieldProps = {
+  field: Field;
+};
+
+export const RadioField = ({ field }: RadioFieldProps) => {
+  let parsedFieldMeta: TRadioFieldMeta | undefined = undefined;
+
+  if (field.fieldMeta) {
+    parsedFieldMeta = ZRadioFieldMeta.parse(field.fieldMeta);
+  }
+
+  if (parsedFieldMeta && (!parsedFieldMeta.values || parsedFieldMeta.values.length === 0)) {
+    return (
+      <FieldIcon fieldMeta={field.fieldMeta} type={field.type} signerEmail={field.signerEmail} />
+    );
+  }
+
+  return (
+    <div className='flex flex-col gap-y-2'>
+      {!parsedFieldMeta?.values ? (
+        <FieldIcon fieldMeta={field.fieldMeta} type={field.type} signerEmail={field.signerEmail} />
+      ) : (
+        <RadioGroup>
+          {parsedFieldMeta.values?.map((item, index) => (
+            <div key={index} className="flex items-center gap-x-1.5">
+              <RadioGroupItem
+                className="pointer-events-none"
+                value={item.value}
+                id={`option-${index}`}
+                checked={item.checked}
+              />
+              <Label htmlFor={`option-${index}`}>{item.value}</Label>
+            </div>
+          ))}
+        </RadioGroup>
+      )}
+    </div>
+  );
+};
diff --git a/packages/ui/primitives/document-flow/document-flow-root.tsx b/packages/ui/primitives/document-flow/document-flow-root.tsx
index 74a232e1d..bdf1fa744 100644
--- a/packages/ui/primitives/document-flow/document-flow-root.tsx
+++ b/packages/ui/primitives/document-flow/document-flow-root.tsx
@@ -126,6 +126,7 @@ export type DocumentFlowFormContainerActionsProps = {
   onGoNextClick?: () => void;
   loading?: boolean;
   disabled?: boolean;
+  disableNextStep?: boolean;
 };
 
 export const DocumentFlowFormContainerActions = ({
@@ -137,6 +138,7 @@ export const DocumentFlowFormContainerActions = ({
   onGoNextClick,
   loading,
   disabled,
+  disableNextStep = false,
 }: DocumentFlowFormContainerActionsProps) => {
   return (
     <div className="mt-4 flex gap-x-4">
@@ -155,7 +157,7 @@ export const DocumentFlowFormContainerActions = ({
         type="button"
         className="bg-documenso flex-1"
         size="lg"
-        disabled={disabled || loading || !canGoNext}
+        disabled={disabled || disableNextStep || loading || !canGoNext}
         loading={loading}
         onClick={onGoNextClick}
       >
diff --git a/packages/ui/primitives/document-flow/field-icon.tsx b/packages/ui/primitives/document-flow/field-icon.tsx
new file mode 100644
index 000000000..3d605d70b
--- /dev/null
+++ b/packages/ui/primitives/document-flow/field-icon.tsx
@@ -0,0 +1,65 @@
+import { CalendarDays, CheckSquare, ChevronDown, Disc, Hash, Mail, Type, User } from 'lucide-react';
+
+import type { TFieldMetaSchema as FieldMetaType } from '@documenso/lib/types/field-meta';
+import { FieldType } from '@documenso/prisma/client';
+
+import { cn } from '../../lib/utils';
+
+type FieldIconProps = {
+  fieldMeta: FieldMetaType;
+  type: FieldType;
+  signerEmail?: string;
+  fontCaveatClassName?: string;
+};
+
+const fieldIcons = {
+  [FieldType.EMAIL]: { icon: Mail, label: 'Email' },
+  [FieldType.NAME]: { icon: User, label: 'Name' },
+  [FieldType.DATE]: { icon: CalendarDays, label: 'Date' },
+  [FieldType.TEXT]: { icon: Type, label: 'Add text' },
+  [FieldType.NUMBER]: { icon: Hash, label: 'Add number' },
+  [FieldType.RADIO]: { icon: Disc, label: 'Radio' },
+  [FieldType.CHECKBOX]: { icon: CheckSquare, label: 'Checkbox' },
+  [FieldType.DROPDOWN]: { icon: ChevronDown, label: 'Select' },
+};
+
+export const FieldIcon = ({
+  fieldMeta,
+  type,
+  signerEmail,
+  fontCaveatClassName,
+}: FieldIconProps) => {
+  if (type === 'SIGNATURE' || type === 'FREE_SIGNATURE') {
+    return (
+      <div
+        className={cn(
+          'text-field-card-foreground flex items-center justify-center gap-x-1 text-xl',
+          fontCaveatClassName,
+        )}
+      >
+        Signature
+      </div>
+    );
+  } else {
+    const Icon = fieldIcons[type]?.icon;
+    let label;
+
+    if (fieldMeta && (type === 'TEXT' || type === 'NUMBER')) {
+      if (type === 'TEXT' && 'text' in fieldMeta && fieldMeta.text && !fieldMeta.label) {
+        label = fieldMeta.text.length > 10 ? fieldMeta.text.substring(0, 10) + '...' : fieldMeta.text;
+      } else if (fieldMeta.label) {
+        label = fieldMeta.label.length > 10 ? fieldMeta.label.substring(0, 10) + '...' : fieldMeta.label;
+      } else {
+        label = fieldIcons[type]?.label;
+      }
+    } else {
+      label = fieldIcons[type]?.label;
+    }
+
+    return (
+      <div className="text-field-card-foreground flex items-center justify-center gap-x-1.5 text-sm">
+        <Icon className='h-4 w-4' /> {label}
+      </div>
+    );
+  }
+};
diff --git a/packages/ui/primitives/document-flow/field-item-advanced-settings.tsx b/packages/ui/primitives/document-flow/field-item-advanced-settings.tsx
new file mode 100644
index 000000000..19616038d
--- /dev/null
+++ b/packages/ui/primitives/document-flow/field-item-advanced-settings.tsx
@@ -0,0 +1,303 @@
+'use client';
+
+import { forwardRef, useEffect, useState } from 'react';
+
+import { useParams } from 'next/navigation';
+import { usePathname } from 'next/navigation';
+
+import { match } from 'ts-pattern';
+
+import {
+  type TBaseFieldMeta as BaseFieldMeta,
+  type TCheckboxFieldMeta as CheckboxFieldMeta,
+  type TDropdownFieldMeta as DropdownFieldMeta,
+  type TFieldMetaSchema as FieldMeta,
+  type TNumberFieldMeta as NumberFieldMeta,
+  type TRadioFieldMeta as RadioFieldMeta,
+  type TTextFieldMeta as TextFieldMeta,
+  ZFieldMetaSchema,
+} from '@documenso/lib/types/field-meta';
+import { FieldType } from '@documenso/prisma/client';
+import { trpc } from '@documenso/trpc/react';
+import { useToast } from '@documenso/ui/primitives/use-toast';
+
+import type { FieldFormType } from './add-fields';
+import {
+  DocumentFlowFormContainerActions,
+  DocumentFlowFormContainerContent,
+  DocumentFlowFormContainerFooter,
+  DocumentFlowFormContainerHeader,
+} from './document-flow-root';
+import { FieldItem } from './field-item';
+import { CheckboxFieldAdvancedSettings } from './field-items-advanced-settings/checkbox-field';
+import { DropdownFieldAdvancedSettings } from './field-items-advanced-settings/dropdown-field';
+import { NumberFieldAdvancedSettings } from './field-items-advanced-settings/number-field';
+import { RadioFieldAdvancedSettings } from './field-items-advanced-settings/radio-field';
+import { TextFieldAdvancedSettings } from './field-items-advanced-settings/text-field';
+
+export type FieldAdvancedSettingsProps = {
+  teamId?: number;
+  title: string;
+  description: string;
+  field: FieldFormType;
+  fields: FieldFormType[];
+  onAdvancedSettings?: () => void;
+  isDocumentPdfLoaded?: boolean;
+  onSave?: (fieldState: FieldMeta) => void;
+};
+
+export type FieldMetaKeys =
+  | keyof BaseFieldMeta
+  | keyof TextFieldMeta
+  | keyof NumberFieldMeta
+  | keyof RadioFieldMeta
+  | keyof CheckboxFieldMeta
+  | keyof DropdownFieldMeta;
+
+const getDefaultState = (fieldType: FieldType): FieldMeta => {
+  switch (fieldType) {
+    case FieldType.TEXT:
+      return {
+        type: 'text',
+        label: '',
+        placeholder: '',
+        text: '',
+        characterLimit: 0,
+        required: false,
+        readOnly: false,
+      };
+    case FieldType.NUMBER:
+      return {
+        type: 'number',
+        label: '',
+        placeholder: '',
+        numberFormat: '',
+        value: '0',
+        minValue: 0,
+        maxValue: 0,
+        required: false,
+        readOnly: false,
+      };
+    case FieldType.RADIO:
+      return {
+        type: 'radio',
+        values: [],
+        required: false,
+        readOnly: false,
+      };
+    case FieldType.CHECKBOX:
+      return {
+        type: 'checkbox',
+        values: [],
+        validationRule: '',
+        validationLength: 0,
+        required: false,
+        readOnly: false,
+      };
+    case FieldType.DROPDOWN:
+      return {
+        type: 'dropdown',
+        values: [],
+        defaultValue: '',
+        required: false,
+        readOnly: false,
+      };
+    default:
+      throw new Error(`Unsupported field type: ${fieldType}`);
+  }
+};
+
+export const FieldAdvancedSettings = forwardRef<HTMLDivElement, FieldAdvancedSettingsProps>(
+  (
+    {
+      title,
+      description,
+      field,
+      fields,
+      onAdvancedSettings,
+      isDocumentPdfLoaded = true,
+      onSave,
+      teamId,
+    },
+    ref,
+  ) => {
+    const { toast } = useToast();
+    const params = useParams();
+    const pathname = usePathname();
+    const id = params?.id;
+    const isTemplatePage = pathname?.includes('template');
+    const isDocumentPage = pathname?.includes('document');
+    const [errors, setErrors] = useState<string[]>([]);
+
+    const { data: template } = trpc.template.getTemplateWithDetailsById.useQuery(
+      {
+        id: Number(id),
+      },
+      {
+        enabled: isTemplatePage,
+      },
+    );
+
+    const { data: document } = trpc.document.getDocumentById.useQuery(
+      {
+        id: Number(id),
+        teamId,
+      },
+      {
+        enabled: isDocumentPage,
+      },
+    );
+
+    const doesFieldExist = (!!document || !!template) && field.nativeId !== undefined;
+
+    const { data: fieldData } = trpc.field.getField.useQuery(
+      {
+        fieldId: Number(field.nativeId),
+        teamId,
+      },
+      {
+        enabled: doesFieldExist,
+      },
+    );
+
+    const fieldMeta = fieldData?.fieldMeta;
+
+    const localStorageKey = `field_${field.formId}_${field.type}`;
+
+    const defaultState: FieldMeta = getDefaultState(field.type);
+
+    const [fieldState, setFieldState] = useState(() => {
+      const savedState = localStorage.getItem(localStorageKey);
+      return savedState ? { ...defaultState, ...JSON.parse(savedState) } : defaultState;
+    });
+
+    useEffect(() => {
+      if (fieldMeta && typeof fieldMeta === 'object') {
+        const parsedFieldMeta = ZFieldMetaSchema.parse(fieldMeta);
+
+        setFieldState({
+          ...defaultState,
+          ...parsedFieldMeta,
+        });
+      }
+      // eslint-disable-next-line react-hooks/exhaustive-deps
+    }, [fieldMeta]);
+
+    const handleFieldChange = (
+      key: FieldMetaKeys,
+      value: string | { checked: boolean; value: string }[] | { value: string }[] | boolean,
+    ) => {
+      setFieldState((prevState: FieldMeta) => {
+        if (['characterLimit', 'minValue', 'maxValue', 'validationLength'].includes(key)) {
+          const parsedValue = Number(value);
+
+          return {
+            ...prevState,
+            [key]: isNaN(parsedValue) ? undefined : parsedValue,
+          };
+        } else {
+          return {
+            ...prevState,
+            [key]: value,
+          };
+        }
+      });
+    };
+
+    const handleOnGoNextClick = () => {
+      try {
+        if (errors.length > 0) {
+          return;
+        } else {
+          localStorage.setItem(localStorageKey, JSON.stringify(fieldState));
+
+          onSave?.(fieldState);
+          onAdvancedSettings?.();
+        }
+      } catch (error) {
+        console.error('Failed to save to localStorage:', error);
+
+        toast({
+          title: 'Error',
+          description: 'Failed to save settings.',
+          variant: 'destructive',
+        });
+      }
+    };
+
+    return (
+      <div ref={ref} className="flex h-full flex-col">
+        <DocumentFlowFormContainerHeader title={title} description={description} />
+        <DocumentFlowFormContainerContent>
+          {isDocumentPdfLoaded &&
+            fields.map((field, index) => (
+              <span key={index} className="opacity-75 active:pointer-events-none">
+                <FieldItem key={index} field={field} disabled={true} />
+              </span>
+            ))}
+
+          {match(field.type)
+            .with(FieldType.TEXT, () => (
+              <TextFieldAdvancedSettings
+                fieldState={fieldState}
+                handleFieldChange={handleFieldChange}
+                handleErrors={setErrors}
+              />
+            ))
+            .with(FieldType.NUMBER, () => (
+              <NumberFieldAdvancedSettings
+                fieldState={fieldState}
+                handleFieldChange={handleFieldChange}
+                handleErrors={setErrors}
+              />
+            ))
+            .with(FieldType.RADIO, () => (
+              <RadioFieldAdvancedSettings
+                fieldState={fieldState}
+                handleFieldChange={handleFieldChange}
+                handleErrors={setErrors}
+              />
+            ))
+            .with(FieldType.CHECKBOX, () => (
+              <CheckboxFieldAdvancedSettings
+                fieldState={fieldState}
+                handleFieldChange={handleFieldChange}
+                handleErrors={setErrors}
+              />
+            ))
+            .with(FieldType.DROPDOWN, () => (
+              <DropdownFieldAdvancedSettings
+                fieldState={fieldState}
+                handleFieldChange={handleFieldChange}
+                handleErrors={setErrors}
+              />
+            ))
+            .otherwise(() => null)}
+
+          {errors.length > 0 && (
+            <div className="mt-4">
+              <ul>
+                {errors.map((error, index) => (
+                  <li className="text-sm text-red-500" key={index}>
+                    {error}
+                  </li>
+                ))}
+              </ul>
+            </div>
+          )}
+        </DocumentFlowFormContainerContent>
+        <DocumentFlowFormContainerFooter className="mt-auto">
+          <DocumentFlowFormContainerActions
+            goNextLabel="Save"
+            goBackLabel="Cancel"
+            onGoBackClick={onAdvancedSettings}
+            onGoNextClick={handleOnGoNextClick}
+            disableNextStep={errors.length > 0}
+          />
+        </DocumentFlowFormContainerFooter>
+      </div>
+    );
+  },
+);
+
+FieldAdvancedSettings.displayName = 'FieldAdvancedSettings';
diff --git a/packages/ui/primitives/document-flow/field-item.tsx b/packages/ui/primitives/document-flow/field-item.tsx
index 9c2d5092c..6e322d868 100644
--- a/packages/ui/primitives/document-flow/field-item.tsx
+++ b/packages/ui/primitives/document-flow/field-item.tsx
@@ -1,20 +1,34 @@
 'use client';
 
-import { useCallback, useEffect, useState } from 'react';
+import { useCallback, useEffect, useMemo, useRef, useState } from 'react';
 
-import { Trash } from 'lucide-react';
+import { Caveat } from 'next/font/google';
+
+import { Settings2, Trash } from 'lucide-react';
 import { createPortal } from 'react-dom';
 import { Rnd } from 'react-rnd';
+import { match } from 'ts-pattern';
 
 import { PDF_VIEWER_PAGE_SELECTOR } from '@documenso/lib/constants/pdf-viewer';
+import type { TFieldMetaSchema } from '@documenso/lib/types/field-meta';
+import { ZCheckboxFieldMeta, ZRadioFieldMeta } from '@documenso/lib/types/field-meta';
 
+import { useSignerColors } from '../../lib/signer-colors';
 import { cn } from '../../lib/utils';
-import { Card, CardContent } from '../card';
+import { CheckboxField } from './advanced-fields/checkbox';
+import { RadioField } from './advanced-fields/radio';
+import { FieldIcon } from './field-icon';
 import type { TDocumentFlowFormSchema } from './types';
-import { FRIENDLY_FIELD_TYPE } from './types';
 
 type Field = TDocumentFlowFormSchema['fields'][0];
 
+const fontCaveat = Caveat({
+  weight: ['500'],
+  subsets: ['latin'],
+  display: 'swap',
+  variable: '--font-caveat',
+});
+
 export type FieldItemProps = {
   field: Field;
   passive?: boolean;
@@ -24,17 +38,23 @@ export type FieldItemProps = {
   onResize?: (_node: HTMLElement) => void;
   onMove?: (_node: HTMLElement) => void;
   onRemove?: () => void;
+  onAdvancedSettings?: () => void;
+  recipientIndex?: number;
+  hideRecipients?: boolean;
 };
 
 export const FieldItem = ({
   field,
   passive,
   disabled,
-  minHeight: _minHeight,
-  minWidth: _minWidth,
+  minHeight,
+  minWidth,
   onResize,
   onMove,
   onRemove,
+  onAdvancedSettings,
+  recipientIndex = 0,
+  hideRecipients = false,
 }: FieldItemProps) => {
   const [active, setActive] = useState(false);
   const [coords, setCoords] = useState({
@@ -43,6 +63,12 @@ export const FieldItem = ({
     pageHeight: 0,
     pageWidth: 0,
   });
+  const [settingsActive, setSettingsActive] = useState(false);
+  const $el = useRef(null);
+
+  const signerStyles = useSignerColors(recipientIndex);
+
+  const advancedField = ['NUMBER', 'RADIO', 'CHECKBOX', 'DROPDOWN', 'TEXT'].includes(field.type);
 
   const calculateCoords = useCallback(() => {
     const $page = document.querySelector<HTMLElement>(
@@ -89,25 +115,63 @@ export const FieldItem = ({
     };
   }, [calculateCoords]);
 
+  const handleClickOutsideField = (event: MouseEvent) => {
+    if (settingsActive && $el.current && !event.composedPath().includes($el.current)) {
+      setSettingsActive(false);
+    }
+  };
+
+  useEffect(() => {
+    document.body.addEventListener('click', handleClickOutsideField);
+    return () => {
+      document.body.removeEventListener('click', handleClickOutsideField);
+    };
+  }, [settingsActive]);
+
+  const hasFieldMetaValues = (
+    fieldType: string,
+    fieldMeta: TFieldMetaSchema,
+    parser: typeof ZCheckboxFieldMeta | typeof ZRadioFieldMeta,
+  ) => {
+    if (field.type !== fieldType || !fieldMeta) {
+      return false;
+    }
+
+    const parsedMeta = parser?.parse(fieldMeta);
+    return parsedMeta && parsedMeta.values && parsedMeta.values.length > 0;
+  };
+
+  const checkBoxHasValues = useMemo(
+    () => hasFieldMetaValues('CHECKBOX', field.fieldMeta, ZCheckboxFieldMeta),
+    [field.fieldMeta],
+  );
+  const radioHasValues = useMemo(
+    () => hasFieldMetaValues('RADIO', field.fieldMeta, ZRadioFieldMeta),
+    [field.fieldMeta],
+  );
+
+  const fixedSize = checkBoxHasValues || radioHasValues;
+
   return createPortal(
     <Rnd
       key={coords.pageX + coords.pageY + coords.pageHeight + coords.pageWidth}
-      className={cn('z-20', {
+      className={cn('group z-20', {
         'pointer-events-none': passive,
-        'pointer-events-none opacity-75': disabled,
+        'pointer-events-none cursor-not-allowed opacity-75': disabled,
         'z-10': !active || disabled,
       })}
-      // minHeight={minHeight}
-      // minWidth={minWidth}
+      minHeight={fixedSize ? '' : minHeight || 'auto'}
+      minWidth={fixedSize ? '' : minWidth || 'auto'}
       default={{
         x: coords.pageX,
         y: coords.pageY,
-        height: coords.pageHeight,
-        width: coords.pageWidth,
+        height: fixedSize ? '' : coords.pageHeight,
+        width: fixedSize ? '' : coords.pageWidth,
       }}
       bounds={`${PDF_VIEWER_PAGE_SELECTOR}[data-page-number="${field.pageNumber}"]`}
       onDragStart={() => setActive(true)}
       onResizeStart={() => setActive(true)}
+      enableResizing={!fixedSize}
       onResizeStop={(_e, _d, ref) => {
         setActive(false);
         onResize?.(ref);
@@ -117,35 +181,69 @@ export const FieldItem = ({
         onMove?.(d.node);
       }}
     >
-      {!disabled && (
-        <button
-          className="text-muted-foreground/50 hover:text-muted-foreground/80 bg-background absolute -right-2 -top-2 z-20 flex h-8 w-8 items-center justify-center rounded-full border"
-          onClick={() => onRemove?.()}
-          onTouchEnd={() => onRemove?.()}
-        >
-          <Trash className="h-4 w-4" />
-        </button>
-      )}
-
-      <Card
-        className={cn('bg-field-card/80 h-full w-full backdrop-blur-[1px]', {
-          'border-field-card-border': !disabled,
-          'border-field-card-border/80': active,
-        })}
+      <div
+        className={cn(
+          'relative flex h-full w-full items-center justify-center bg-white',
+          signerStyles.default.base,
+          signerStyles.default.fieldItem,
+        )}
+        onClick={() => {
+          setSettingsActive((prev) => !prev);
+        }}
+        ref={$el}
       >
-        <CardContent
-          className={cn(
-            'text-field-card-foreground flex h-full w-full flex-col items-center justify-center p-2',
-            {
-              'text-field-card-foreground/50': disabled,
-            },
-          )}
-        >
-          {FRIENDLY_FIELD_TYPE[field.type]}
+        {match(field.type)
+          .with('CHECKBOX', () => <CheckboxField field={field} />)
+          .with('RADIO', () => <RadioField field={field} />)
+          .otherwise(() => (
+            <FieldIcon
+              fieldMeta={field.fieldMeta}
+              type={field.type}
+              signerEmail={field.signerEmail}
+              fontCaveatClassName={fontCaveat.className}
+            />
+          ))}
 
-          <p className="w-full truncate text-center text-xs">{field.signerEmail}</p>
-        </CardContent>
-      </Card>
+        {!hideRecipients && (
+          <div className="absolute -right-6 top-0 z-20 hidden h-full w-6 items-center justify-center group-hover:flex">
+            <div
+              className={cn(
+                'flex h-7 w-6 flex-col items-center justify-center rounded-r-lg text-[0.625rem] font-bold text-white',
+                signerStyles.default.fieldItemInitials,
+                {
+                  '!opacity-50': disabled || passive,
+                },
+              )}
+            >
+              {(field.signerEmail?.charAt(0)?.toUpperCase() ?? '') +
+                (field.signerEmail?.charAt(1)?.toUpperCase() ?? '')}
+            </div>
+          </div>
+        )}
+      </div>
+
+      {!disabled && settingsActive && (
+        <div className="mt-1 flex justify-center">
+          <div className="dark:bg-background group flex items-center justify-evenly rounded-md border gap-x-1 bg-gray-900 p-0.5">
+            {advancedField && (
+              <button
+                className="dark:text-muted-foreground/50 dark:hover:text-muted-foreground dark:hover:bg-foreground/10 rounded-sm p-1.5 text-gray-400 transition-colors hover:bg-white/10 hover:text-gray-100"
+                onClick={onAdvancedSettings}
+                onTouchEnd={onAdvancedSettings}
+              >
+                <Settings2 className="h-3 w-3" />
+              </button>
+            )}
+            <button
+              className="dark:text-muted-foreground/50 dark:hover:text-muted-foreground dark:hover:bg-foreground/10 rounded-sm p-1.5 text-gray-400 transition-colors hover:bg-white/10 hover:text-gray-100"
+              onClick={onRemove}
+              onTouchEnd={onRemove}
+            >
+              <Trash className="h-3 w-3" />
+            </button>
+          </div>
+        </div>
+      )}
     </Rnd>,
     document.body,
   );
diff --git a/packages/ui/primitives/document-flow/field-items-advanced-settings/checkbox-field.tsx b/packages/ui/primitives/document-flow/field-items-advanced-settings/checkbox-field.tsx
new file mode 100644
index 000000000..5723ddc80
--- /dev/null
+++ b/packages/ui/primitives/document-flow/field-items-advanced-settings/checkbox-field.tsx
@@ -0,0 +1,224 @@
+'use client';
+
+import { useEffect, useState } from 'react';
+
+import { ChevronDown, ChevronUp, Trash } from 'lucide-react';
+
+import { validateCheckboxField } from '@documenso/lib/advanced-fields-validation/validate-checkbox';
+import { type TCheckboxFieldMeta as CheckboxFieldMeta } from '@documenso/lib/types/field-meta';
+import { Button } from '@documenso/ui/primitives/button';
+import { Checkbox } from '@documenso/ui/primitives/checkbox';
+import { Input } from '@documenso/ui/primitives/input';
+import { Label } from '@documenso/ui/primitives/label';
+import {
+  Select,
+  SelectContent,
+  SelectItem,
+  SelectTrigger,
+  SelectValue,
+} from '@documenso/ui/primitives/select';
+import { Switch } from '@documenso/ui/primitives/switch';
+
+import { checkboxValidationLength, checkboxValidationRules } from './constants';
+
+type CheckboxFieldAdvancedSettingsProps = {
+  fieldState: CheckboxFieldMeta;
+  handleFieldChange: (
+    key: keyof CheckboxFieldMeta,
+    value: string | { checked: boolean; value: string }[] | boolean,
+  ) => void;
+  handleErrors: (errors: string[]) => void;
+};
+
+export const CheckboxFieldAdvancedSettings = ({
+  fieldState,
+  handleFieldChange,
+  handleErrors,
+}: CheckboxFieldAdvancedSettingsProps) => {
+  const [showValidation, setShowValidation] = useState(false);
+  const [values, setValues] = useState(fieldState.values ?? [{ id: 1, checked: false, value: '' }]);
+  const [readOnly, setReadOnly] = useState(fieldState.readOnly ?? false);
+  const [required, setRequired] = useState(fieldState.required ?? false);
+  const [validationLength, setValidationLength] = useState(fieldState.validationLength ?? 0);
+  const [validationRule, setValidationRule] = useState(fieldState.validationRule ?? '');
+
+  const handleToggleChange = (field: keyof CheckboxFieldMeta, value: string | boolean) => {
+    const readOnly = field === 'readOnly' ? Boolean(value) : Boolean(fieldState.readOnly);
+    const required = field === 'required' ? Boolean(value) : Boolean(fieldState.required);
+    const validationRule =
+      field === 'validationRule' ? String(value) : String(fieldState.validationRule);
+    const validationLength =
+      field === 'validationLength' ? Number(value) : Number(fieldState.validationLength);
+
+    setReadOnly(readOnly);
+    setRequired(required);
+    setValidationRule(validationRule);
+    setValidationLength(validationLength);
+
+    const errors = validateCheckboxField(
+      values.map((item) => item.value),
+      {
+        readOnly,
+        required,
+        validationRule,
+        validationLength,
+      },
+    );
+    handleErrors(errors);
+
+    handleFieldChange(field, value);
+  };
+
+  const addValue = () => {
+    const newId = values.length > 0 ? Math.max(...values.map((val) => val.id)) + 1 : 1;
+    setValues([...values, { id: newId, checked: false, value: '' }]);
+  };
+
+  useEffect(() => {
+    const errors = validateCheckboxField(
+      values.map((item) => item.value),
+      {
+        readOnly,
+        required,
+        validationRule,
+        validationLength,
+      },
+    );
+    handleErrors(errors);
+    handleFieldChange('values', values);
+  }, [values]);
+
+  const removeValue = (index: number) => {
+    if (values.length === 1) return;
+
+    const newValues = [...values];
+    newValues.splice(index, 1);
+    setValues(newValues);
+    handleFieldChange('values', newValues);
+  };
+
+  const handleCheckboxValue = (
+    index: number,
+    property: 'value' | 'checked',
+    newValue: string | boolean,
+  ) => {
+    const newValues = [...values];
+
+    if (property === 'checked') {
+      newValues[index].checked = Boolean(newValue);
+    } else if (property === 'value') {
+      newValues[index].value = String(newValue);
+    }
+
+    setValues(newValues);
+    handleFieldChange('values', newValues);
+  };
+
+  useEffect(() => {
+    setValues(fieldState.values ?? [{ id: 1, checked: false, value: '' }]);
+  }, [fieldState.values]);
+
+  return (
+    <div className="flex flex-col gap-4">
+      <div className="flex flex-row items-center gap-x-4">
+        <div className="flex w-2/3 flex-col">
+          <Label>Validation</Label>
+          <Select
+            value={fieldState.validationRule}
+            onValueChange={(val) => handleToggleChange('validationRule', val)}
+          >
+            <SelectTrigger className="text-muted-foreground bg-background mt-2 w-full">
+              <SelectValue placeholder="Select at least" />
+            </SelectTrigger>
+            <SelectContent position="popper">
+              {checkboxValidationRules.map((item, index) => (
+                <SelectItem key={index} value={item}>
+                  {item}
+                </SelectItem>
+              ))}
+            </SelectContent>
+          </Select>
+        </div>
+        <div className="mt-3 flex w-1/3 flex-col">
+          <Select
+            value={fieldState.validationLength ? String(fieldState.validationLength) : ''}
+            onValueChange={(val) => handleToggleChange('validationLength', val)}
+          >
+            <SelectTrigger className="text-muted-foreground bg-background mt-2 w-full">
+              <SelectValue placeholder="Pick a number" />
+            </SelectTrigger>
+            <SelectContent position="popper">
+              {checkboxValidationLength.map((item, index) => (
+                <SelectItem key={index} value={String(item)}>
+                  {item}
+                </SelectItem>
+              ))}
+            </SelectContent>
+          </Select>
+        </div>
+      </div>
+      <div className="flex flex-col gap-4">
+        <div className="flex flex-row items-center gap-2">
+          <Switch
+            className="bg-background"
+            checked={fieldState.required}
+            onCheckedChange={(checked) => handleToggleChange('required', checked)}
+          />
+          <Label>Required field</Label>
+        </div>
+        <div className="flex flex-row items-center gap-2">
+          <Switch
+            className="bg-background"
+            checked={fieldState.readOnly}
+            onCheckedChange={(checked) => handleToggleChange('readOnly', checked)}
+          />
+          <Label>Read only</Label>
+        </div>
+      </div>
+      <Button
+        className="bg-foreground/10 hover:bg-foreground/5 border-foreground/10 mt-2 border"
+        variant="outline"
+        onClick={() => setShowValidation((prev) => !prev)}
+      >
+        <span className="flex w-full flex-row justify-between">
+          <span className="flex items-center">Checkbox values</span>
+          {showValidation ? <ChevronUp /> : <ChevronDown />}
+        </span>
+      </Button>
+
+      {showValidation && (
+        <div>
+          {values.map((value, index) => (
+            <div key={index} className="mt-2 flex items-center gap-4">
+              <Checkbox
+                className="data-[state=checked]:bg-documenso border-foreground/30 h-5 w-5"
+                checkClassName="text-white"
+                checked={value.checked}
+                onCheckedChange={(checked) => handleCheckboxValue(index, 'checked', checked)}
+              />
+              <Input
+                className="w-1/2"
+                value={value.value}
+                onChange={(e) => handleCheckboxValue(index, 'value', e.target.value)}
+              />
+              <button
+                type="button"
+                className="col-span-1 mt-auto inline-flex h-10 w-10 items-center  text-slate-500 hover:opacity-80 disabled:cursor-not-allowed disabled:opacity-50"
+                onClick={() => removeValue(index)}
+              >
+                <Trash className="h-5 w-5" />
+              </button>
+            </div>
+          ))}
+          <Button
+            className="bg-foreground/10 hover:bg-foreground/5 border-foreground/10 ml-9 mt-4 border"
+            variant="outline"
+            onClick={addValue}
+          >
+            Add another value
+          </Button>
+        </div>
+      )}
+    </div>
+  );
+};
diff --git a/packages/ui/primitives/document-flow/field-items-advanced-settings/constants.ts b/packages/ui/primitives/document-flow/field-items-advanced-settings/constants.ts
new file mode 100644
index 000000000..6916c6825
--- /dev/null
+++ b/packages/ui/primitives/document-flow/field-items-advanced-settings/constants.ts
@@ -0,0 +1,31 @@
+export const numberFormatValues = [
+  {
+    label: '123,456,789.00',
+    value: '123,456,789.00',
+  },
+  {
+    label: '123.456.789,00',
+    value: '123.456.789,00',
+  },
+  {
+    label: '123456,789.00',
+    value: '123456,789.00',
+  },
+];
+
+export const checkboxValidationRules = ['Select at least', 'Select exactly', 'Select at most'];
+export const checkboxValidationLength = [1, 2, 3, 4, 5, 6, 7, 8, 9, 10];
+export const checkboxValidationSigns = [
+  {
+    label: 'Select at least',
+    value: '>=',
+  },
+  {
+    label: 'Select exactly',
+    value: '=',
+  },
+  {
+    label: 'Select at most',
+    value: '<=',
+  },
+];
diff --git a/packages/ui/primitives/document-flow/field-items-advanced-settings/dropdown-field.tsx b/packages/ui/primitives/document-flow/field-items-advanced-settings/dropdown-field.tsx
new file mode 100644
index 000000000..d4aebc151
--- /dev/null
+++ b/packages/ui/primitives/document-flow/field-items-advanced-settings/dropdown-field.tsx
@@ -0,0 +1,171 @@
+'use client';
+
+import { useEffect, useState } from 'react';
+
+import { ChevronDown, ChevronUp, Trash } from 'lucide-react';
+
+import { validateDropdownField } from '@documenso/lib/advanced-fields-validation/validate-dropdown';
+import { type TDropdownFieldMeta as DropdownFieldMeta } from '@documenso/lib/types/field-meta';
+import { Button } from '@documenso/ui/primitives/button';
+import { Input } from '@documenso/ui/primitives/input';
+import { Label } from '@documenso/ui/primitives/label';
+import {
+  Select,
+  SelectContent,
+  SelectItem,
+  SelectTrigger,
+  SelectValue,
+} from '@documenso/ui/primitives/select';
+import { Switch } from '@documenso/ui/primitives/switch';
+
+type DropdownFieldAdvancedSettingsProps = {
+  fieldState: DropdownFieldMeta;
+  handleFieldChange: (
+    key: keyof DropdownFieldMeta,
+    value: string | { value: string }[] | boolean,
+  ) => void;
+  handleErrors: (errors: string[]) => void;
+};
+
+export const DropdownFieldAdvancedSettings = ({
+  fieldState,
+  handleFieldChange,
+  handleErrors,
+}: DropdownFieldAdvancedSettingsProps) => {
+  const [showValidation, setShowValidation] = useState(false);
+  const [values, setValues] = useState(fieldState.values ?? [{ value: 'Option 1' }]);
+  const [readOnly, setReadOnly] = useState(fieldState.readOnly ?? false);
+  const [required, setRequired] = useState(fieldState.required ?? false);
+  const [defaultValue, setDefaultValue] = useState(fieldState.defaultValue ?? 'Option 1');
+
+  const addValue = () => {
+    setValues([...values, { value: 'New option' }]);
+    handleFieldChange('values', [...values, { value: 'New option' }]);
+  };
+
+  const removeValue = (index: number) => {
+    if (values.length === 1) return;
+
+    const newValues = [...values];
+    newValues.splice(index, 1);
+    setValues(newValues);
+    handleFieldChange('values', newValues);
+  };
+
+  const handleToggleChange = (field: keyof DropdownFieldMeta, value: string | boolean) => {
+    const readOnly = field === 'readOnly' ? Boolean(value) : Boolean(fieldState.readOnly);
+    const required = field === 'required' ? Boolean(value) : Boolean(fieldState.required);
+    setReadOnly(readOnly);
+    setRequired(required);
+
+    const errors = validateDropdownField(undefined, { readOnly, required, values });
+    handleErrors(errors);
+
+    handleFieldChange(field, value);
+  };
+
+  const handleValueChange = (index: number, newValue: string) => {
+    const updatedValues = [...values];
+    updatedValues[index].value = newValue;
+    setValues(updatedValues);
+    handleFieldChange('values', updatedValues);
+  };
+
+  useEffect(() => {
+    const errors = validateDropdownField(undefined, { readOnly, required, values });
+    handleErrors(errors);
+  }, [values]);
+
+  useEffect(() => {
+    setValues(fieldState.values ?? [{ value: 'Option 1' }]);
+  }, [fieldState.values]);
+
+  useEffect(() => {
+    setDefaultValue(fieldState.defaultValue ?? 'Option 1');
+  }, [fieldState.defaultValue]);
+
+  return (
+    <div className="text-dark flex flex-col gap-4">
+      <div>
+        <Label>Select default option</Label>
+        <Select
+          defaultValue={defaultValue}
+          onValueChange={(val) => {
+            setDefaultValue(val);
+            handleFieldChange('defaultValue', val);
+          }}
+        >
+          <SelectTrigger className="text-muted-foreground bg-background mt-2 w-full">
+            <SelectValue defaultValue={defaultValue} placeholder="-- Select --" />
+          </SelectTrigger>
+          <SelectContent position="popper">
+            {values.map((item, index) => (
+              <SelectItem
+                key={index}
+                value={item.value && item.value.length > 0 ? item.value.toString() : String(index)}
+              >
+                {item.value}
+              </SelectItem>
+            ))}
+          </SelectContent>
+        </Select>
+      </div>
+      <div className="flex flex-col gap-4">
+        <div className="flex flex-row items-center gap-2">
+          <Switch
+            className="bg-background"
+            checked={fieldState.required}
+            onCheckedChange={(checked) => handleToggleChange('required', checked)}
+          />
+          <Label>Required field</Label>
+        </div>
+        <div className="flex flex-row items-center gap-2">
+          <Switch
+            className="bg-background"
+            checked={fieldState.readOnly}
+            onCheckedChange={(checked) => handleToggleChange('readOnly', checked)}
+          />
+          <Label>Read only</Label>
+        </div>
+      </div>
+      <Button
+        className="bg-foreground/10 hover:bg-foreground/5 border-foreground/10 mt-2 border"
+        variant="outline"
+        onClick={() => setShowValidation((prev) => !prev)}
+      >
+        <span className="flex w-full flex-row justify-between">
+          <span className="flex items-center">Dropdown options</span>
+          {showValidation ? <ChevronUp /> : <ChevronDown />}
+        </span>
+      </Button>
+
+      {showValidation && (
+        <div>
+          {values.map((value, index) => (
+            <div key={index} className="mt-2 flex items-center gap-4">
+              <Input
+                className="w-1/2"
+                value={value.value}
+                onChange={(e) => handleValueChange(index, e.target.value)}
+              />
+              <button
+                type="button"
+                className="col-span-1 mt-auto inline-flex h-10 w-10 items-center  text-slate-500 hover:opacity-80 disabled:cursor-not-allowed disabled:opacity-50"
+                onClick={() => removeValue(index)}
+              >
+                <Trash className="h-5 w-5" />
+              </button>
+            </div>
+          ))}
+          <Button
+            className="bg-foreground/10 hover:bg-foreground/5 border-foreground/10 ml-9 mt-4 border"
+            variant="outline"
+            onClick={addValue}
+          >
+            Add another option
+          </Button>
+        </div>
+      )}
+    </div>
+  );
+};
diff --git a/packages/ui/primitives/document-flow/field-items-advanced-settings/number-field.tsx b/packages/ui/primitives/document-flow/field-items-advanced-settings/number-field.tsx
new file mode 100644
index 000000000..d6ead593c
--- /dev/null
+++ b/packages/ui/primitives/document-flow/field-items-advanced-settings/number-field.tsx
@@ -0,0 +1,160 @@
+'use client';
+
+import { useState } from 'react';
+
+import { ChevronDown, ChevronUp } from 'lucide-react';
+
+import { validateNumberField } from '@documenso/lib/advanced-fields-validation/validate-number';
+import { type TNumberFieldMeta as NumberFieldMeta } from '@documenso/lib/types/field-meta';
+import { Button } from '@documenso/ui/primitives/button';
+import { Input } from '@documenso/ui/primitives/input';
+import { Label } from '@documenso/ui/primitives/label';
+import {
+  Select,
+  SelectContent,
+  SelectItem,
+  SelectTrigger,
+  SelectValue,
+} from '@documenso/ui/primitives/select';
+import { Switch } from '@documenso/ui/primitives/switch';
+
+import { numberFormatValues } from './constants';
+
+type NumberFieldAdvancedSettingsProps = {
+  fieldState: NumberFieldMeta;
+  handleFieldChange: (key: keyof NumberFieldMeta, value: string | boolean) => void;
+  handleErrors: (errors: string[]) => void;
+};
+
+export const NumberFieldAdvancedSettings = ({
+  fieldState,
+  handleFieldChange,
+  handleErrors,
+}: NumberFieldAdvancedSettingsProps) => {
+  const [showValidation, setShowValidation] = useState(false);
+
+  const handleInput = (field: keyof NumberFieldMeta, value: string | boolean) => {
+    const userValue = field === 'value' ? value : fieldState.value || 0;
+    const userMinValue = field === 'minValue' ? Number(value) : Number(fieldState.minValue || 0);
+    const userMaxValue = field === 'maxValue' ? Number(value) : Number(fieldState.maxValue || 0);
+    const readOnly = field === 'readOnly' ? Boolean(value) : Boolean(fieldState.readOnly);
+    const required = field === 'required' ? Boolean(value) : Boolean(fieldState.required);
+    const numberFormat = field === 'numberFormat' ? String(value) : fieldState.numberFormat || '';
+
+    const valueErrors = validateNumberField(String(userValue), {
+      minValue: userMinValue,
+      maxValue: userMaxValue,
+      readOnly,
+      required,
+      numberFormat,
+    });
+    handleErrors(valueErrors);
+
+    handleFieldChange(field, value);
+  };
+
+  return (
+    <div className="flex flex-col gap-4">
+      <div>
+        <Label>Label</Label>
+        <Input
+          id="label"
+          className="bg-background mt-2"
+          placeholder="Label"
+          value={fieldState.label}
+          onChange={(e) => handleFieldChange('label', e.target.value)}
+        />
+      </div>
+      <div>
+        <Label className="mt-4">Placeholder</Label>
+        <Input
+          id="placeholder"
+          className="bg-background mt-2"
+          placeholder="Placeholder"
+          value={fieldState.placeholder}
+          onChange={(e) => handleFieldChange('placeholder', e.target.value)}
+        />
+      </div>
+      <div>
+        <Label className="mt-4">Value</Label>
+        <Input
+          id="value"
+          className="bg-background mt-2"
+          placeholder="Value"
+          value={fieldState.value}
+          onChange={(e) => handleInput('value', e.target.value)}
+        />
+      </div>
+      <div>
+        <Label>Number format</Label>
+        <Select
+          value={fieldState.numberFormat}
+          onValueChange={(val) => handleInput('numberFormat', val)}
+        >
+          <SelectTrigger className="text-muted-foreground bg-background mt-2 w-full">
+            <SelectValue placeholder="Field format" />
+          </SelectTrigger>
+          <SelectContent position="popper">
+            {numberFormatValues.map((item, index) => (
+              <SelectItem key={index} value={item.value}>
+                {item.label}
+              </SelectItem>
+            ))}
+          </SelectContent>
+        </Select>
+      </div>
+      <div className="mt-2 flex flex-col gap-4">
+        <div className="flex flex-row items-center gap-2">
+          <Switch
+            className="bg-background"
+            checked={fieldState.required}
+            onCheckedChange={(checked) => handleInput('required', checked)}
+          />
+          <Label>Required field</Label>
+        </div>
+        <div className="flex flex-row items-center gap-2">
+          <Switch
+            className="bg-background"
+            checked={fieldState.readOnly}
+            onCheckedChange={(checked) => handleInput('readOnly', checked)}
+          />
+          <Label>Read only</Label>
+        </div>
+      </div>
+      <Button
+        className="bg-foreground/10 hover:bg-foreground/5 border-foreground/10 mt-2 border"
+        variant="outline"
+        onClick={() => setShowValidation((prev) => !prev)}
+      >
+        <span className="flex w-full flex-row justify-between">
+          <span className="flex items-center">Validation</span>
+          {showValidation ? <ChevronUp /> : <ChevronDown />}
+        </span>
+      </Button>
+      {showValidation && (
+        <div className="mb-4 flex flex-row gap-x-4">
+          <div className="flex flex-col">
+            <Label className="mt-4">Min</Label>
+            <Input
+              id="minValue"
+              className="bg-background mt-2"
+              placeholder="E.g. 0"
+              value={fieldState.minValue}
+              onChange={(e) => handleInput('minValue', e.target.value)}
+            />
+          </div>
+          <div className="flex flex-col">
+            <Label className="mt-4">Max</Label>
+            <Input
+              id="maxValue"
+              className="bg-background mt-2"
+              placeholder="E.g. 100"
+              value={fieldState.maxValue}
+              onChange={(e) => handleInput('maxValue', e.target.value)}
+            />
+          </div>
+        </div>
+      )}
+    </div>
+  );
+};
diff --git a/packages/ui/primitives/document-flow/field-items-advanced-settings/radio-field.tsx b/packages/ui/primitives/document-flow/field-items-advanced-settings/radio-field.tsx
new file mode 100644
index 000000000..ea499e85a
--- /dev/null
+++ b/packages/ui/primitives/document-flow/field-items-advanced-settings/radio-field.tsx
@@ -0,0 +1,166 @@
+'use client';
+
+import { useEffect, useState } from 'react';
+
+import { ChevronDown, ChevronUp, Trash } from 'lucide-react';
+
+import { validateRadioField } from '@documenso/lib/advanced-fields-validation/validate-radio';
+import { type TRadioFieldMeta as RadioFieldMeta } from '@documenso/lib/types/field-meta';
+import { Button } from '@documenso/ui/primitives/button';
+import { Checkbox } from '@documenso/ui/primitives/checkbox';
+import { Input } from '@documenso/ui/primitives/input';
+import { Label } from '@documenso/ui/primitives/label';
+import { Switch } from '@documenso/ui/primitives/switch';
+
+export type RadioFieldAdvancedSettingsProps = {
+  fieldState: RadioFieldMeta;
+  handleFieldChange: (
+    key: keyof RadioFieldMeta,
+    value: string | { checked: boolean; value: string }[] | boolean,
+  ) => void;
+  handleErrors: (errors: string[]) => void;
+};
+
+export const RadioFieldAdvancedSettings = ({
+  fieldState,
+  handleFieldChange,
+  handleErrors,
+}: RadioFieldAdvancedSettingsProps) => {
+  const [showValidation, setShowValidation] = useState(false);
+  const [values, setValues] = useState(
+    fieldState.values ?? [{ id: 1, checked: false, value: 'Default value' }],
+  );
+  const [readOnly, setReadOnly] = useState(fieldState.readOnly ?? false);
+  const [required, setRequired] = useState(fieldState.required ?? false);
+
+  const addValue = () => {
+    const newId = values.length > 0 ? Math.max(...values.map((val) => val.id)) + 1 : 1;
+    const newValue = { id: newId, checked: false, value: '' };
+    const updatedValues = [...values, newValue];
+
+    setValues(updatedValues);
+    handleFieldChange('values', updatedValues);
+  };
+
+  const removeValue = (id: number) => {
+    if (values.length === 1) return;
+
+    const newValues = values.filter((val) => val.id !== id);
+    setValues(newValues);
+    handleFieldChange('values', newValues);
+  };
+
+  const handleCheckedChange = (checked: boolean, id: number) => {
+    const newValues = values.map((val) => {
+      if (val.id === id) {
+        return { ...val, checked: Boolean(checked) };
+      } else {
+        return { ...val, checked: false };
+      }
+    });
+
+    setValues(newValues);
+    handleFieldChange('values', newValues);
+  };
+
+  const handleToggleChange = (field: keyof RadioFieldMeta, value: string | boolean) => {
+    const readOnly = field === 'readOnly' ? Boolean(value) : Boolean(fieldState.readOnly);
+    const required = field === 'required' ? Boolean(value) : Boolean(fieldState.required);
+    setReadOnly(readOnly);
+    setRequired(required);
+
+    const errors = validateRadioField(String(value), { readOnly, required, values });
+    handleErrors(errors);
+
+    handleFieldChange(field, value);
+  };
+
+  const handleInputChange = (value: string, id: number) => {
+    const newValues = values.map((val) => {
+      if (val.id === id) {
+        return { ...val, value };
+      }
+      return val;
+    });
+
+    setValues(newValues);
+    handleFieldChange('values', newValues);
+
+    return newValues;
+  };
+
+  useEffect(() => {
+    setValues(fieldState.values ?? [{ id: 1, checked: false, value: 'Default value' }]);
+  }, [fieldState.values]);
+
+  useEffect(() => {
+    const errors = validateRadioField(undefined, { readOnly, required, values });
+    handleErrors(errors);
+  }, [values]);
+
+  return (
+    <div className="flex flex-col gap-4">
+      <div className="flex flex-col gap-4">
+        <div className="flex flex-row items-center gap-2">
+          <Switch
+            className="bg-background"
+            checked={fieldState.required}
+            onCheckedChange={(checked) => handleToggleChange('required', checked)}
+          />
+          <Label>Required field</Label>
+        </div>
+        <div className="flex flex-row items-center gap-2">
+          <Switch
+            className="bg-background"
+            checked={fieldState.readOnly}
+            onCheckedChange={(checked) => handleToggleChange('readOnly', checked)}
+          />
+          <Label>Read only</Label>
+        </div>
+      </div>
+      <Button
+        className="bg-foreground/10 hover:bg-foreground/5 border-foreground/10 mt-2 border"
+        variant="outline"
+        onClick={() => setShowValidation((prev) => !prev)}
+      >
+        <span className="flex w-full flex-row justify-between">
+          <span className="flex items-center">Radio values</span>
+          {showValidation ? <ChevronUp /> : <ChevronDown />}
+        </span>
+      </Button>
+
+      {showValidation && (
+        <div>
+          {values.map((value) => (
+            <div key={value.id} className="mt-2 flex items-center gap-4">
+              <Checkbox
+                className="data-[state=checked]:bg-documenso border-foreground/30 data-[state=checked]:ring-documenso dark:data-[state=checked]:ring-offset-background h-5 w-5 rounded-full data-[state=checked]:ring-1 data-[state=checked]:ring-offset-2 data-[state=checked]:ring-offset-white"
+                checked={value.checked}
+                onCheckedChange={(checked) => handleCheckedChange(Boolean(checked), value.id)}
+              />
+              <Input
+                className="w-1/2"
+                value={value.value}
+                onChange={(e) => handleInputChange(e.target.value, value.id)}
+              />
+              <button
+                type="button"
+                className="col-span-1 mt-auto inline-flex h-10 w-10 items-center text-slate-500 hover:opacity-80 disabled:cursor-not-allowed disabled:opacity-50 dark:text-white"
+                onClick={() => removeValue(value.id)}
+              >
+                <Trash className="h-5 w-5" />
+              </button>
+            </div>
+          ))}
+          <Button
+            className="bg-foreground/10 hover:bg-foreground/5 border-foreground/10 ml-9 mt-4 border"
+            variant="outline"
+            onClick={addValue}
+          >
+            Add another value
+          </Button>
+        </div>
+      )}
+    </div>
+  );
+};
diff --git a/packages/ui/primitives/document-flow/field-items-advanced-settings/text-field.tsx b/packages/ui/primitives/document-flow/field-items-advanced-settings/text-field.tsx
new file mode 100644
index 000000000..34d6ee9f0
--- /dev/null
+++ b/packages/ui/primitives/document-flow/field-items-advanced-settings/text-field.tsx
@@ -0,0 +1,103 @@
+import { validateTextField } from '@documenso/lib/advanced-fields-validation/validate-text';
+import { type TTextFieldMeta as TextFieldMeta } from '@documenso/lib/types/field-meta';
+import { Input } from '@documenso/ui/primitives/input';
+import { Label } from '@documenso/ui/primitives/label';
+import { Switch } from '@documenso/ui/primitives/switch';
+import { Textarea } from '@documenso/ui/primitives/textarea';
+
+type TextFieldAdvancedSettingsProps = {
+  fieldState: TextFieldMeta;
+  handleFieldChange: (key: keyof TextFieldMeta, value: string | boolean) => void;
+  handleErrors: (errors: string[]) => void;
+};
+
+export const TextFieldAdvancedSettings = ({
+  fieldState,
+  handleFieldChange,
+  handleErrors,
+}: TextFieldAdvancedSettingsProps) => {
+  const handleInput = (field: keyof TextFieldMeta, value: string | boolean) => {
+    const text = field === 'text' ? String(value) : fieldState.text || '';
+    const limit =
+      field === 'characterLimit' ? Number(value) : Number(fieldState.characterLimit || 0);
+    const readOnly = field === 'readOnly' ? Boolean(value) : Boolean(fieldState.readOnly);
+    const required = field === 'required' ? Boolean(value) : Boolean(fieldState.required);
+
+    const textErrors = validateTextField(text, {
+      characterLimit: Number(limit),
+      readOnly,
+      required,
+    });
+
+    handleErrors(textErrors);
+    handleFieldChange(field, value);
+  };
+
+  return (
+    <div className="flex flex-col gap-4">
+      <div>
+        <Label>Label</Label>
+        <Input
+          id="label"
+          className="bg-background mt-2"
+          placeholder="Field label"
+          value={fieldState.label}
+          onChange={(e) => handleFieldChange('label', e.target.value)}
+        />
+      </div>
+      <div>
+        <Label className="mt-4">Placeholder</Label>
+        <Input
+          id="placeholder"
+          className="bg-background mt-2"
+          placeholder="Field placeholder"
+          value={fieldState.placeholder}
+          onChange={(e) => handleFieldChange('placeholder', e.target.value)}
+        />
+      </div>
+
+      <div>
+        <Label className="mt-4">Add text</Label>
+        <Textarea
+          id="text"
+          className="bg-background mt-2"
+          placeholder="Add text to the field"
+          value={fieldState.text}
+          onChange={(e) => handleInput('text', e.target.value)}
+        />
+      </div>
+
+      <div>
+        <Label>Character Limit</Label>
+        <Input
+          id="characterLimit"
+          type="number"
+          min={0}
+          className="bg-background mt-2"
+          placeholder="Field character limit"
+          value={fieldState.characterLimit}
+          onChange={(e) => handleInput('characterLimit', e.target.value)}
+        />
+      </div>
+
+      <div className="mt-4 flex flex-col gap-4">
+        <div className="flex flex-row items-center gap-2">
+          <Switch
+            className="bg-background"
+            checked={fieldState.required}
+            onCheckedChange={(checked) => handleInput('required', checked)}
+          />
+          <Label>Required field</Label>
+        </div>
+        <div className="flex flex-row items-center gap-2">
+          <Switch
+            className="bg-background"
+            checked={fieldState.readOnly}
+            onCheckedChange={(checked) => handleInput('readOnly', checked)}
+          />
+          <Label>Read only</Label>
+        </div>
+      </div>
+    </div>
+  );
+};
diff --git a/packages/ui/primitives/document-flow/single-player-mode-fields.tsx b/packages/ui/primitives/document-flow/single-player-mode-fields.tsx
index 2ef115e4b..7b707fadd 100644
--- a/packages/ui/primitives/document-flow/single-player-mode-fields.tsx
+++ b/packages/ui/primitives/document-flow/single-player-mode-fields.tsx
@@ -2,7 +2,10 @@
 
 import React, { useRef } from 'react';
 
+import { Caveat } from 'next/font/google';
+
 import { AnimatePresence, motion } from 'framer-motion';
+import { CalendarDays, CheckSquare, ChevronDown, Disc, Hash, Mail, Type, User } from 'lucide-react';
 import { match } from 'ts-pattern';
 
 import { useElementScaleSize } from '@documenso/lib/client-only/hooks/use-element-scale-size';
@@ -18,6 +21,14 @@ import { FieldType } from '@documenso/prisma/client';
 import type { FieldWithSignature } from '@documenso/prisma/types/field-with-signature';
 
 import { FieldRootContainer } from '../../components/field/field';
+import { cn } from '../../lib/utils';
+
+const fontCaveat = Caveat({
+  weight: ['500'],
+  subsets: ['latin'],
+  display: 'swap',
+  variable: '--font-caveat',
+});
 
 export type SinglePlayerModeFieldContainerProps = {
   field: FieldWithSignature;
@@ -110,9 +121,11 @@ export function SinglePlayerModeSignatureField({
       ) : (
         <button
           onClick={() => onClick?.()}
-          className="group-hover:text-primary text-muted-foreground absolute inset-0 h-full w-full duration-200"
+          className={
+            cn('group-hover:text-primary absolute inset-0 h-full w-full duration-200', fontCaveat.className)
+          }
         >
-          Signature
+          <span className="text-muted-foreground truncate text-3xl font-medium ">Signature</span>
         </button>
       )}
     </SinglePlayerModeFieldCardContainer>
@@ -152,32 +165,82 @@ export function SinglePlayerModeCustomTextField({
   const fontSize = maxFontSize * scalingFactor;
 
   return (
-    <SinglePlayerModeFieldCardContainer field={field}>
-      {field.inserted ? (
-        <p
-          ref={$paragraphEl}
-          style={{
-            fontSize: `clamp(${minFontSize}px, ${fontSize}px, ${maxFontSize}px)`,
-            fontFamily: `var(${fontVariable})`,
-          }}
-        >
-          {field.customText}
-        </p>
-      ) : (
-        <button
-          onClick={() => onClick?.()}
-          className="group-hover:text-primary text-muted-foreground absolute inset-0 h-full w-full text-lg duration-200"
-        >
-          {match(field.type)
-            .with(FieldType.DATE, () => 'Date')
-            .with(FieldType.NAME, () => 'Name')
-            .with(FieldType.EMAIL, () => 'Email')
-            .with(FieldType.TEXT, () => 'Text')
-            .with(FieldType.SIGNATURE, FieldType.FREE_SIGNATURE, () => 'Signature')
-            .otherwise(() => '')}
-        </button>
-      )}
-    </SinglePlayerModeFieldCardContainer>
+    <>
+      <SinglePlayerModeFieldCardContainer field={field}>
+        {field.inserted ? (
+          <p
+            ref={$paragraphEl}
+            style={{
+              fontSize: `clamp(${minFontSize}px, ${fontSize}px, ${maxFontSize}px)`,
+              fontFamily: `var(${fontVariable})`,
+            }}
+          >
+            {field.customText ??
+              (field.fieldMeta && typeof field.fieldMeta === 'object' && 'label' in field.fieldMeta
+                ? field.fieldMeta.label
+                : '')}
+          </p>
+        ) : (
+          <button
+            onClick={() => onClick?.()}
+            className="group-hover:text-primary text-muted-foreground absolute inset-0 h-full w-full text-lg duration-200"
+          >
+            {match(field.type)
+              .with(FieldType.DATE, () => (
+                <div className="text-field-card-foreground flex items-center justify-center gap-x-1 text-xl font-light">
+                  <CalendarDays /> Date
+                </div>
+              ))
+              .with(FieldType.NAME, () => (
+                <div className="text-field-card-foreground flex items-center justify-center gap-x-1 text-xl font-light">
+                  <User /> Name
+                </div>
+              ))
+              .with(FieldType.EMAIL, () => (
+                <div className="text-field-card-foreground flex items-center justify-center gap-x-1 text-xl font-light">
+                  <Mail /> Email
+                </div>
+              ))
+              .with(FieldType.TEXT, () => (
+                <div className="text-field-card-foreground flex items-center justify-center gap-x-1 text-xl font-light">
+                  <Type /> Text
+                </div>
+              ))
+              .with(FieldType.SIGNATURE, FieldType.FREE_SIGNATURE, () => (
+                <div
+                  className={cn(
+                    'text-muted-foreground w-full truncate text-3xl font-medium',
+                    fontCaveat.className,
+                  )}
+                >
+                  Signature
+                </div>
+              ))
+              .with(FieldType.NUMBER, () => (
+                <div className="text-field-card-foreground flex items-center justify-center gap-x-1 text-xl font-light">
+                  <Hash /> Number
+                </div>
+              ))
+              .with(FieldType.CHECKBOX, () => (
+                <div className="text-field-card-foreground flex items-center justify-center gap-x-1 text-xl font-light">
+                  <CheckSquare /> Checkbox
+                </div>
+              ))
+              .with(FieldType.RADIO, () => (
+                <div className="text-field-card-foreground flex items-center justify-center gap-x-1 text-xl font-light">
+                  <Disc /> Radio
+                </div>
+              ))
+              .with(FieldType.DROPDOWN, () => (
+                <div className="text-field-card-foreground flex items-center justify-center gap-x-1 text-xl font-light">
+                  <ChevronDown /> Dropdown
+                </div>
+              ))
+              .otherwise(() => '')}
+          </button>
+        )}
+      </SinglePlayerModeFieldCardContainer>
+    </>
   );
 }
 
diff --git a/packages/ui/primitives/document-flow/types.ts b/packages/ui/primitives/document-flow/types.ts
index 82f5706e6..9614ac3e9 100644
--- a/packages/ui/primitives/document-flow/types.ts
+++ b/packages/ui/primitives/document-flow/types.ts
@@ -1,5 +1,6 @@
 import { z } from 'zod';
 
+import { ZFieldMetaSchema } from '@documenso/lib/types/field-meta';
 import { FieldType } from '@documenso/prisma/client';
 
 export const ZDocumentFlowFormSchema = z.object({
@@ -30,6 +31,7 @@ export const ZDocumentFlowFormSchema = z.object({
       pageY: z.number().min(0),
       pageWidth: z.number().min(0),
       pageHeight: z.number().min(0),
+      fieldMeta: ZFieldMetaSchema,
     }),
   ),
 
@@ -48,6 +50,10 @@ export const FRIENDLY_FIELD_TYPE: Record<FieldType, string> = {
   [FieldType.DATE]: 'Date',
   [FieldType.EMAIL]: 'Email',
   [FieldType.NAME]: 'Name',
+  [FieldType.NUMBER]: 'Number',
+  [FieldType.RADIO]: 'Radio',
+  [FieldType.CHECKBOX]: 'Checkbox',
+  [FieldType.DROPDOWN]: 'Select',
 };
 
 export interface DocumentFlowStep {
diff --git a/packages/ui/primitives/template-flow/add-template-fields.tsx b/packages/ui/primitives/template-flow/add-template-fields.tsx
index b09d740f5..1500f4d89 100644
--- a/packages/ui/primitives/template-flow/add-template-fields.tsx
+++ b/packages/ui/primitives/template-flow/add-template-fields.tsx
@@ -4,13 +4,27 @@ import { useCallback, useEffect, useMemo, useRef, useState } from 'react';
 
 import { Caveat } from 'next/font/google';
 
-import { ChevronsUpDown } from 'lucide-react';
+import {
+  CalendarDays,
+  CheckSquare,
+  ChevronDown,
+  ChevronsUpDown,
+  Disc,
+  Hash,
+  Mail,
+  Type,
+  User,
+} from 'lucide-react';
 import { useFieldArray, useForm } from 'react-hook-form';
 
 import { getBoundingClientRect } from '@documenso/lib/client-only/get-bounding-client-rect';
 import { useDocumentElement } from '@documenso/lib/client-only/hooks/use-document-element';
 import { PDF_VIEWER_PAGE_SELECTOR } from '@documenso/lib/constants/pdf-viewer';
 import { RECIPIENT_ROLES_DESCRIPTION } from '@documenso/lib/constants/recipient-roles';
+import {
+  type TFieldMetaSchema as FieldMeta,
+  ZFieldMetaSchema,
+} from '@documenso/lib/types/field-meta';
 import { nanoid } from '@documenso/lib/universal/id';
 import type { Field, Recipient } from '@documenso/prisma/client';
 import { FieldType, RecipientRole } from '@documenso/prisma/client';
@@ -28,6 +42,7 @@ import {
   DocumentFlowFormContainerActions,
   DocumentFlowFormContainerContent,
   DocumentFlowFormContainerFooter,
+  DocumentFlowFormContainerHeader,
   DocumentFlowFormContainerStep,
 } from '@documenso/ui/primitives/document-flow/document-flow-root';
 import { FieldItem } from '@documenso/ui/primitives/document-flow/field-item';
@@ -35,8 +50,10 @@ import type { DocumentFlowStep } from '@documenso/ui/primitives/document-flow/ty
 import { FRIENDLY_FIELD_TYPE } from '@documenso/ui/primitives/document-flow/types';
 import { Popover, PopoverContent, PopoverTrigger } from '@documenso/ui/primitives/popover';
 
+import { getSignerColorStyles, useSignerColors } from '../../lib/signer-colors';
+import type { FieldFormType } from '../document-flow/add-fields';
+import { FieldAdvancedSettings } from '../document-flow/field-item-advanced-settings';
 import { useStep } from '../stepper';
-// import { Tooltip, TooltipContent, TooltipTrigger } from '@documenso/ui/primitives/tooltip';
 import type { TAddTemplateFieldsFormSchema } from './add-template-fields.types';
 
 const fontCaveat = Caveat({
@@ -46,11 +63,8 @@ const fontCaveat = Caveat({
   variable: '--font-caveat',
 });
 
-const DEFAULT_HEIGHT_PERCENT = 5;
-const DEFAULT_WIDTH_PERCENT = 15;
-
-const MIN_HEIGHT_PX = 60;
-const MIN_WIDTH_PX = 200;
+const MIN_HEIGHT_PX = 40;
+const MIN_WIDTH_PX = 140;
 
 export type AddTemplateFieldsFormProps = {
   documentFlow: DocumentFlowStep;
@@ -58,6 +72,7 @@ export type AddTemplateFieldsFormProps = {
   recipients: Recipient[];
   fields: Field[];
   onSubmit: (_data: TAddTemplateFieldsFormSchema) => void;
+  teamId?: number;
 };
 
 export const AddTemplateFieldsFormPartial = ({
@@ -66,15 +81,19 @@ export const AddTemplateFieldsFormPartial = ({
   recipients,
   fields,
   onSubmit,
+  teamId,
 }: AddTemplateFieldsFormProps) => {
   const { isWithinPageBounds, getFieldPosition, getPage } = useDocumentElement();
-
   const { currentStep, totalSteps, previousStep } = useStep();
+  const [showAdvancedSettings, setShowAdvancedSettings] = useState(false);
+  const [currentField, setCurrentField] = useState<FieldFormType>();
 
   const {
     control,
     handleSubmit,
     formState: { isSubmitting },
+    setValue,
+    getValues,
   } = useForm<TAddTemplateFieldsFormSchema>({
     defaultValues: {
       fields: fields.map((field) => ({
@@ -97,6 +116,25 @@ export const AddTemplateFieldsFormPartial = ({
 
   const onFormSubmit = handleSubmit(onSubmit);
 
+  const handleSavedFieldSettings = (fieldState: FieldMeta) => {
+    const initialValues = getValues();
+
+    const updatedFields = initialValues.fields.map((field) => {
+      if (field.formId === currentField?.formId) {
+        const parsedFieldMeta = ZFieldMetaSchema.parse(fieldState);
+
+        return {
+          ...field,
+          fieldMeta: parsedFieldMeta,
+        };
+      }
+
+      return field;
+    });
+
+    setValue('fields', updatedFields);
+  };
+
   const {
     append,
     remove,
@@ -111,6 +149,11 @@ export const AddTemplateFieldsFormPartial = ({
   const [selectedSigner, setSelectedSigner] = useState<Recipient | null>(null);
   const [showRecipientsSelector, setShowRecipientsSelector] = useState(false);
 
+  const selectedSignerIndex = recipients.findIndex((r) => r.id === selectedSigner?.id);
+  const selectedSignerStyles = useSignerColors(
+    selectedSignerIndex === -1 ? 0 : selectedSignerIndex,
+  );
+
   const [isFieldWithinBounds, setIsFieldWithinBounds] = useState(false);
   const [coords, setCoords] = useState({
     x: 0,
@@ -189,6 +232,7 @@ export const AddTemplateFieldsFormPartial = ({
         signerEmail: selectedSigner.email,
         signerId: selectedSigner.id,
         signerToken: selectedSigner.token ?? '',
+        fieldMeta: undefined,
       });
 
       setIsFieldWithinBounds(false);
@@ -270,11 +314,9 @@ export const AddTemplateFieldsFormPartial = ({
         return;
       }
 
-      const { height, width } = $page.getBoundingClientRect();
-
       fieldBounds.current = {
-        height: Math.max(height * (DEFAULT_HEIGHT_PERCENT / 100), MIN_HEIGHT_PX),
-        width: Math.max(width * (DEFAULT_WIDTH_PERCENT / 100), MIN_WIDTH_PX),
+        height: Math.max(MIN_HEIGHT_PX),
+        width: Math.max(MIN_WIDTH_PX),
       };
     });
 
@@ -314,265 +356,428 @@ export const AddTemplateFieldsFormPartial = ({
     );
   }, [recipientsByRole]);
 
+  const handleAdvancedSettings = () => {
+    setShowAdvancedSettings((prev) => !prev);
+  };
+
   return (
     <>
-      <DocumentFlowFormContainerContent>
-        <div className="flex flex-col">
-          {selectedField && (
-            <Card
-              className={cn(
-                'bg-background pointer-events-none fixed z-50 cursor-pointer transition-opacity',
-                {
-                  'border-primary': isFieldWithinBounds,
-                  'opacity-50': !isFieldWithinBounds,
-                },
-              )}
-              style={{
-                top: coords.y,
-                left: coords.x,
-                height: fieldBounds.current.height,
-                width: fieldBounds.current.width,
-              }}
-            >
-              <CardContent className="text-foreground flex h-full w-full items-center justify-center p-2">
-                {FRIENDLY_FIELD_TYPE[selectedField]}
-              </CardContent>
-            </Card>
-          )}
-
-          {localFields.map((field, index) => (
-            <FieldItem
-              key={index}
-              field={field}
-              disabled={selectedSigner?.email !== field.signerEmail}
-              minHeight={fieldBounds.current.height}
-              minWidth={fieldBounds.current.width}
-              passive={isFieldWithinBounds && !!selectedField}
-              onResize={(options) => onFieldResize(options, index)}
-              onMove={(options) => onFieldMove(options, index)}
-              onRemove={() => remove(index)}
-            />
-          ))}
-
-          {!hideRecipients && (
-            <Popover open={showRecipientsSelector} onOpenChange={setShowRecipientsSelector}>
-              <PopoverTrigger asChild>
-                <Button
-                  type="button"
-                  variant="outline"
-                  role="combobox"
-                  className="bg-background text-muted-foreground mb-12 justify-between font-normal"
+      {showAdvancedSettings && currentField ? (
+        <FieldAdvancedSettings
+          title="Advanced settings"
+          description={`Configure the ${FRIENDLY_FIELD_TYPE[currentField.type]} field`}
+          field={currentField}
+          fields={localFields}
+          onAdvancedSettings={handleAdvancedSettings}
+          onSave={handleSavedFieldSettings}
+          teamId={teamId}
+        />
+      ) : (
+        <>
+          <DocumentFlowFormContainerHeader
+            title={documentFlow.title}
+            description={documentFlow.description}
+          />
+          <DocumentFlowFormContainerContent>
+            <div className="flex flex-col">
+              {selectedField && (
+                <div
+                  className={cn(
+                    'pointer-events-none fixed z-50 flex cursor-pointer flex-col items-center justify-center bg-white transition duration-200',
+                    selectedSignerStyles.default.base,
+                    {
+                      '-rotate-6 scale-90 opacity-50': !isFieldWithinBounds,
+                    },
+                  )}
+                  style={{
+                    top: coords.y,
+                    left: coords.x,
+                    height: fieldBounds.current.height,
+                    width: fieldBounds.current.width,
+                  }}
                 >
-                  {selectedSigner?.email && (
-                    <span className="flex-1 truncate text-left">
-                      {selectedSigner?.name} ({selectedSigner?.email})
-                    </span>
-                  )}
+                  {FRIENDLY_FIELD_TYPE[selectedField]}
+                </div>
+              )}
 
-                  {!selectedSigner?.email && (
-                    <span className="flex-1 truncate text-left">{selectedSigner?.email}</span>
-                  )}
+              {localFields.map((field, index) => {
+                const recipientIndex = recipients.findIndex((r) => r.email === field.signerEmail);
 
-                  <ChevronsUpDown className="ml-2 h-4 w-4" />
-                </Button>
-              </PopoverTrigger>
+                return (
+                  <FieldItem
+                    key={index}
+                    recipientIndex={recipientIndex === -1 ? 0 : recipientIndex}
+                    field={field}
+                    disabled={selectedSigner?.email !== field.signerEmail}
+                    minHeight={fieldBounds.current.height}
+                    minWidth={fieldBounds.current.width}
+                    passive={isFieldWithinBounds && !!selectedField}
+                    onResize={(options) => onFieldResize(options, index)}
+                    onMove={(options) => onFieldMove(options, index)}
+                    onRemove={() => remove(index)}
+                    onAdvancedSettings={() => {
+                      setCurrentField(field);
+                      handleAdvancedSettings();
+                    }}
+                    hideRecipients={hideRecipients}
+                  />
+                );
+              })}
 
-              <PopoverContent className="p-0" align="start">
-                <Command>
-                  <CommandInput />
-                  <CommandEmpty>
-                    <span className="text-muted-foreground inline-block px-4">
-                      No recipient matching this description was found.
-                    </span>
-                  </CommandEmpty>
-
-                  {recipientsByRoleToDisplay.map(([role, recipients], roleIndex) => (
-                    <CommandGroup key={roleIndex}>
-                      <div className="text-muted-foreground mb-1 ml-2 mt-2 text-xs font-medium">
-                        {`${RECIPIENT_ROLES_DESCRIPTION[role].roleName}s`}
-                      </div>
-
-                      {recipients.length === 0 && (
-                        <div
-                          key={`${role}-empty`}
-                          className="text-muted-foreground/80 px-4 pb-4 pt-2.5 text-center text-xs"
-                        >
-                          No recipients with this role
-                        </div>
+              {!hideRecipients && (
+                <Popover open={showRecipientsSelector} onOpenChange={setShowRecipientsSelector}>
+                  <PopoverTrigger asChild>
+                    <Button
+                      type="button"
+                      variant="outline"
+                      role="combobox"
+                      className={cn(
+                        'bg-background text-muted-foreground hover:text-foreground mb-12 mt-2 justify-between font-normal',
+                        selectedSignerStyles.default.base,
+                      )}
+                    >
+                      {selectedSigner?.email && (
+                        <span className="flex-1 truncate text-left">
+                          {selectedSigner?.name} ({selectedSigner?.email})
+                        </span>
                       )}
 
-                      {recipients.map((recipient) => (
-                        <CommandItem
-                          key={recipient.id}
-                          className={cn('px-2 last:mb-1 [&:not(:first-child)]:mt-1')}
-                          onSelect={() => {
-                            setSelectedSigner(recipient);
-                            setShowRecipientsSelector(false);
-                          }}
-                        >
-                          <span
-                            className={cn('text-foreground/70 truncate', {
-                              'text-foreground/80': recipient === selectedSigner,
-                            })}
-                          >
-                            {recipient.name && (
-                              <span title={`${recipient.name} (${recipient.email})`}>
-                                {recipient.name} ({recipient.email})
+                      {!selectedSigner?.email && (
+                        <span className="gradie flex-1 truncate text-left">
+                          {selectedSigner?.email}
+                        </span>
+                      )}
+
+                      <ChevronsUpDown className="ml-2 h-4 w-4" />
+                    </Button>
+                  </PopoverTrigger>
+
+                  <PopoverContent className="p-0" align="start">
+                    <Command value={selectedSigner?.email}>
+                      <CommandInput />
+
+                      <CommandEmpty>
+                        <span className="text-muted-foreground inline-block px-4">
+                          No recipient matching this description was found.
+                        </span>
+                      </CommandEmpty>
+
+                      {recipientsByRoleToDisplay.map(([role, roleRecipients], roleIndex) => (
+                        <CommandGroup key={roleIndex}>
+                          <div className="text-muted-foreground mb-1 ml-2 mt-2 text-xs font-medium">
+                            {`${RECIPIENT_ROLES_DESCRIPTION[role].roleName}s`}
+                          </div>
+
+                          {roleRecipients.length === 0 && (
+                            <div
+                              key={`${role}-empty`}
+                              className="text-muted-foreground/80 px-4 pb-4 pt-2.5 text-center text-xs"
+                            >
+                              No recipients with this role
+                            </div>
+                          )}
+
+                          {roleRecipients.map((recipient) => (
+                            <CommandItem
+                              key={recipient.id}
+                              className={cn(
+                                'px-2 last:mb-1 [&:not(:first-child)]:mt-1',
+                                getSignerColorStyles(
+                                  Math.max(
+                                    recipients.findIndex((r) => r.id === recipient.id),
+                                    0,
+                                  ),
+                                ).default.comboxBoxItem,
+                              )}
+                              onSelect={() => {
+                                setSelectedSigner(recipient);
+                                setShowRecipientsSelector(false);
+                              }}
+                            >
+                              <span
+                                className={cn('text-foreground/70 truncate', {
+                                  'text-foreground/80': recipient === selectedSigner,
+                                })}
+                              >
+                                {recipient.name && (
+                                  <span title={`${recipient.name} (${recipient.email})`}>
+                                    {recipient.name} ({recipient.email})
+                                  </span>
+                                )}
+
+                                {!recipient.name && (
+                                  <span title={recipient.email}>{recipient.email}</span>
+                                )}
                               </span>
-                            )}
-
-                            {!recipient.name && (
-                              <span title={recipient.email}>{recipient.email}</span>
-                            )}
-                          </span>
-                        </CommandItem>
+                            </CommandItem>
+                          ))}
+                        </CommandGroup>
                       ))}
-                    </CommandGroup>
-                  ))}
-                </Command>
-              </PopoverContent>
-            </Popover>
-          )}
+                    </Command>
+                  </PopoverContent>
+                </Popover>
+              )}
 
-          <div className="-mx-2 flex-1 overflow-y-auto px-2">
-            <div className="grid grid-cols-2 gap-x-4 gap-y-8">
-              <button
-                type="button"
-                className="group h-full w-full"
-                disabled={!selectedSigner}
-                onClick={() => setSelectedField(FieldType.SIGNATURE)}
-                onMouseDown={() => setSelectedField(FieldType.SIGNATURE)}
-                data-selected={selectedField === FieldType.SIGNATURE ? true : undefined}
-              >
-                <Card className="group-data-[selected]:border-documenso h-full w-full cursor-pointer group-disabled:opacity-50">
-                  <CardContent className="flex flex-col items-center justify-center px-6 py-4">
-                    <p
+              <div className="-mx-2 flex-1 overflow-y-auto px-2">
+                <fieldset className="my-2 grid grid-cols-3 gap-4">
+                  <button
+                    type="button"
+                    className="group h-full w-full"
+                    onClick={() => setSelectedField(FieldType.SIGNATURE)}
+                    onMouseDown={() => setSelectedField(FieldType.SIGNATURE)}
+                    data-selected={selectedField === FieldType.SIGNATURE ? true : undefined}
+                  >
+                    <Card
                       className={cn(
-                        'text-muted-foreground group-data-[selected]:text-foreground w-full truncate text-3xl font-medium',
-                        fontCaveat.className,
+                        'flex h-full w-full cursor-pointer items-center justify-center group-disabled:opacity-50',
+                        // selectedSignerStyles.borderClass,
                       )}
                     >
-                      {selectedSigner?.name || 'Signature'}
-                    </p>
+                      <CardContent className="flex flex-col items-center justify-center px-6 py-4">
+                        <p
+                          className={cn(
+                            'text-muted-foreground group-data-[selected]:text-foreground flex items-center justify-center gap-x-1.5 text-lg font-normal',
+                            fontCaveat.className,
+                          )}
+                        >
+                          Signature
+                        </p>
+                      </CardContent>
+                    </Card>
+                  </button>
 
-                    <p className="text-muted-foreground mt-2 text-center text-xs">Signature</p>
-                  </CardContent>
-                </Card>
-              </button>
-
-              <button
-                type="button"
-                className="group h-full w-full"
-                disabled={!selectedSigner}
-                onClick={() => setSelectedField(FieldType.EMAIL)}
-                onMouseDown={() => setSelectedField(FieldType.EMAIL)}
-                data-selected={selectedField === FieldType.EMAIL ? true : undefined}
-              >
-                <Card className="group-data-[selected]:border-documenso h-full w-full cursor-pointer group-disabled:opacity-50">
-                  <CardContent className="flex flex-col items-center justify-center px-6 py-4">
-                    <p
+                  <button
+                    type="button"
+                    className="group h-full w-full"
+                    onClick={() => setSelectedField(FieldType.EMAIL)}
+                    onMouseDown={() => setSelectedField(FieldType.EMAIL)}
+                    data-selected={selectedField === FieldType.EMAIL ? true : undefined}
+                  >
+                    <Card
                       className={cn(
-                        'text-muted-foreground group-data-[selected]:text-foreground text-xl font-medium',
+                        'flex h-full w-full cursor-pointer items-center justify-center group-disabled:opacity-50',
+                        // selectedSignerStyles.borderClass,
                       )}
                     >
-                      {'Email'}
-                    </p>
+                      <CardContent className="p-4">
+                        <p
+                          className={cn(
+                            'text-muted-foreground group-data-[selected]:text-foreground flex items-center justify-center gap-x-1.5 text-sm font-normal',
+                          )}
+                        >
+                          <Mail className="h-4 w-4" />
+                          Email
+                        </p>
+                      </CardContent>
+                    </Card>
+                  </button>
 
-                    <p className="text-muted-foreground mt-2 text-xs">Email</p>
-                  </CardContent>
-                </Card>
-              </button>
-
-              <button
-                type="button"
-                className="group h-full w-full"
-                disabled={!selectedSigner}
-                onClick={() => setSelectedField(FieldType.NAME)}
-                onMouseDown={() => setSelectedField(FieldType.NAME)}
-                data-selected={selectedField === FieldType.NAME ? true : undefined}
-              >
-                <Card className="group-data-[selected]:border-documenso h-full w-full cursor-pointer group-disabled:opacity-50">
-                  <CardContent className="flex flex-col items-center justify-center px-6 py-4">
-                    <p
+                  <button
+                    type="button"
+                    className="group h-full w-full"
+                    onClick={() => setSelectedField(FieldType.NAME)}
+                    onMouseDown={() => setSelectedField(FieldType.NAME)}
+                    data-selected={selectedField === FieldType.NAME ? true : undefined}
+                  >
+                    <Card
                       className={cn(
-                        'text-muted-foreground group-data-[selected]:text-foreground text-xl font-medium',
+                        'flex h-full w-full cursor-pointer items-center justify-center group-disabled:opacity-50',
+                        // selectedSignerStyles.borderClass,
                       )}
                     >
-                      {'Name'}
-                    </p>
+                      <CardContent className="p-4">
+                        <p
+                          className={cn(
+                            'text-muted-foreground group-data-[selected]:text-foreground flex items-center justify-center gap-x-1.5 text-sm font-normal',
+                          )}
+                        >
+                          <User className="h-4 w-4" />
+                          Name
+                        </p>
+                      </CardContent>
+                    </Card>
+                  </button>
 
-                    <p className="text-muted-foreground mt-2 text-xs">Name</p>
-                  </CardContent>
-                </Card>
-              </button>
-
-              <button
-                type="button"
-                className="group h-full w-full"
-                disabled={!selectedSigner}
-                onClick={() => setSelectedField(FieldType.DATE)}
-                onMouseDown={() => setSelectedField(FieldType.DATE)}
-                data-selected={selectedField === FieldType.DATE ? true : undefined}
-              >
-                <Card className="group-data-[selected]:border-documenso h-full w-full cursor-pointer group-disabled:opacity-50">
-                  <CardContent className="flex flex-col items-center justify-center px-6 py-4">
-                    <p
+                  <button
+                    type="button"
+                    className="group h-full w-full"
+                    onClick={() => setSelectedField(FieldType.DATE)}
+                    onMouseDown={() => setSelectedField(FieldType.DATE)}
+                    data-selected={selectedField === FieldType.DATE ? true : undefined}
+                  >
+                    <Card
                       className={cn(
-                        'text-muted-foreground group-data-[selected]:text-foreground text-xl font-medium',
+                        'flex h-full w-full cursor-pointer items-center justify-center group-disabled:opacity-50',
+                        // selectedSignerStyles.borderClass,
                       )}
                     >
-                      {'Date'}
-                    </p>
+                      <CardContent className="p-4">
+                        <p
+                          className={cn(
+                            'text-muted-foreground group-data-[selected]:text-foreground flex items-center justify-center gap-x-1.5 text-sm font-normal',
+                          )}
+                        >
+                          <CalendarDays className="h-4 w-4" />
+                          Date
+                        </p>
+                      </CardContent>
+                    </Card>
+                  </button>
 
-                    <p className="text-muted-foreground mt-2 text-xs">Date</p>
-                  </CardContent>
-                </Card>
-              </button>
-
-              <button
-                type="button"
-                className="group h-full w-full"
-                onClick={() => setSelectedField(FieldType.TEXT)}
-                onMouseDown={() => setSelectedField(FieldType.TEXT)}
-                data-selected={selectedField === FieldType.TEXT ? true : undefined}
-              >
-                <Card className="group-data-[selected]:border-documenso h-full w-full cursor-pointer group-disabled:opacity-50">
-                  <CardContent className="flex flex-col items-center justify-center px-6 py-4">
-                    <p
+                  <button
+                    type="button"
+                    className="group h-full w-full"
+                    onClick={() => setSelectedField(FieldType.TEXT)}
+                    onMouseDown={() => setSelectedField(FieldType.TEXT)}
+                    data-selected={selectedField === FieldType.TEXT ? true : undefined}
+                  >
+                    <Card
                       className={cn(
-                        'text-muted-foreground group-data-[selected]:text-foreground text-xl font-medium',
+                        'flex h-full w-full cursor-pointer items-center justify-center group-disabled:opacity-50',
+                        // selectedSignerStyles.borderClass,
                       )}
                     >
-                      {'Text'}
-                    </p>
+                      <CardContent className="p-4">
+                        <p
+                          className={cn(
+                            'text-muted-foreground group-data-[selected]:text-foreground flex items-center justify-center gap-x-1.5 text-sm font-normal',
+                          )}
+                        >
+                          <Type className="h-4 w-4" />
+                          Text
+                        </p>
+                      </CardContent>
+                    </Card>
+                  </button>
 
-                    <p className="text-muted-foreground mt-2 text-xs">Custom Text</p>
-                  </CardContent>
-                </Card>
-              </button>
+                  <button
+                    type="button"
+                    className="group h-full w-full"
+                    onClick={() => setSelectedField(FieldType.NUMBER)}
+                    onMouseDown={() => setSelectedField(FieldType.NUMBER)}
+                    data-selected={selectedField === FieldType.NUMBER ? true : undefined}
+                  >
+                    <Card
+                      className={cn(
+                        'flex h-full w-full cursor-pointer items-center justify-center group-disabled:opacity-50',
+                        // selectedSignerStyles.borderClass,
+                      )}
+                    >
+                      <CardContent className="p-4">
+                        <p
+                          className={cn(
+                            'text-muted-foreground group-data-[selected]:text-foreground flex items-center justify-center gap-x-1.5 text-sm font-normal',
+                          )}
+                        >
+                          <Hash className="h-4 w-4" />
+                          Number
+                        </p>
+                      </CardContent>
+                    </Card>
+                  </button>
+
+                  <button
+                    type="button"
+                    className="group h-full w-full"
+                    onClick={() => setSelectedField(FieldType.RADIO)}
+                    onMouseDown={() => setSelectedField(FieldType.RADIO)}
+                    data-selected={selectedField === FieldType.RADIO ? true : undefined}
+                  >
+                    <Card
+                      className={cn(
+                        'flex h-full w-full cursor-pointer items-center justify-center group-disabled:opacity-50',
+                        // selectedSignerStyles.borderClass,
+                      )}
+                    >
+                      <CardContent className="p-4">
+                        <p
+                          className={cn(
+                            'text-muted-foreground group-data-[selected]:text-foreground flex items-center justify-center gap-x-1.5 text-sm font-normal',
+                          )}
+                        >
+                          <Disc className="h-4 w-4" />
+                          Radio
+                        </p>
+                      </CardContent>
+                    </Card>
+                  </button>
+
+                  <button
+                    type="button"
+                    className="group h-full w-full"
+                    onClick={() => setSelectedField(FieldType.CHECKBOX)}
+                    onMouseDown={() => setSelectedField(FieldType.CHECKBOX)}
+                    data-selected={selectedField === FieldType.CHECKBOX ? true : undefined}
+                  >
+                    <Card
+                      className={cn(
+                        'flex h-full w-full cursor-pointer items-center justify-center group-disabled:opacity-50',
+                        // selectedSignerStyles.borderClass,
+                      )}
+                    >
+                      <CardContent className="p-4">
+                        <p
+                          className={cn(
+                            'text-muted-foreground group-data-[selected]:text-foreground flex items-center justify-center gap-x-1.5 text-sm font-normal',
+                          )}
+                        >
+                          <CheckSquare className="h-4 w-4" />
+                          Checkbox
+                        </p>
+                      </CardContent>
+                    </Card>
+                  </button>
+
+                  <button
+                    type="button"
+                    className="group h-full w-full"
+                    onClick={() => setSelectedField(FieldType.DROPDOWN)}
+                    onMouseDown={() => setSelectedField(FieldType.DROPDOWN)}
+                    data-selected={selectedField === FieldType.DROPDOWN ? true : undefined}
+                  >
+                    <Card
+                      className={cn(
+                        'flex h-full w-full cursor-pointer items-center justify-center group-disabled:opacity-50',
+                        // selectedSignerStyles.borderClass,
+                      )}
+                    >
+                      <CardContent className="p-4">
+                        <p
+                          className={cn(
+                            'text-muted-foreground group-data-[selected]:text-foreground flex items-center justify-center gap-x-1.5 text-sm font-normal',
+                          )}
+                        >
+                          <ChevronDown className="h-4 w-4" />
+                          Dropdown
+                        </p>
+                      </CardContent>
+                    </Card>
+                  </button>
+                </fieldset>
+              </div>
             </div>
-          </div>
-        </div>
-      </DocumentFlowFormContainerContent>
+          </DocumentFlowFormContainerContent>
 
-      <DocumentFlowFormContainerFooter>
-        <DocumentFlowFormContainerStep
-          title={documentFlow.title}
-          step={currentStep}
-          maxStep={totalSteps}
-        />
+          <DocumentFlowFormContainerFooter>
+            <DocumentFlowFormContainerStep
+              title={documentFlow.title}
+              step={currentStep}
+              maxStep={totalSteps}
+            />
 
-        <DocumentFlowFormContainerActions
-          loading={isSubmitting}
-          disabled={isSubmitting}
-          goNextLabel="Save Template"
-          onGoBackClick={() => {
-            previousStep();
-            remove();
-          }}
-          onGoNextClick={() => void onFormSubmit()}
-        />
-      </DocumentFlowFormContainerFooter>
+            <DocumentFlowFormContainerActions
+              loading={isSubmitting}
+              disabled={isSubmitting}
+              goNextLabel="Save Template"
+              onGoBackClick={() => {
+                previousStep();
+                remove();
+              }}
+              onGoNextClick={() => void onFormSubmit()}
+            />
+          </DocumentFlowFormContainerFooter>
+        </>
+      )}
     </>
   );
 };
diff --git a/packages/ui/primitives/template-flow/add-template-fields.types.ts b/packages/ui/primitives/template-flow/add-template-fields.types.ts
index 4406f82a0..b58af7947 100644
--- a/packages/ui/primitives/template-flow/add-template-fields.types.ts
+++ b/packages/ui/primitives/template-flow/add-template-fields.types.ts
@@ -1,5 +1,6 @@
 import { z } from 'zod';
 
+import { ZFieldMetaSchema } from '@documenso/lib/types/field-meta';
 import { FieldType } from '@documenso/prisma/client';
 
 export const ZAddTemplateFieldsFormSchema = z.object({
@@ -16,6 +17,7 @@ export const ZAddTemplateFieldsFormSchema = z.object({
       pageY: z.number().min(0),
       pageWidth: z.number().min(0),
       pageHeight: z.number().min(0),
+      fieldMeta: ZFieldMetaSchema,
     }),
   ),
 });
diff --git a/packages/ui/primitives/template-flow/add-template-placeholder-recipients.tsx b/packages/ui/primitives/template-flow/add-template-placeholder-recipients.tsx
index d45251e01..2671513ca 100644
--- a/packages/ui/primitives/template-flow/add-template-placeholder-recipients.tsx
+++ b/packages/ui/primitives/template-flow/add-template-placeholder-recipients.tsx
@@ -26,6 +26,7 @@ import {
   DocumentFlowFormContainerActions,
   DocumentFlowFormContainerContent,
   DocumentFlowFormContainerFooter,
+  DocumentFlowFormContainerHeader,
   DocumentFlowFormContainerStep,
 } from '../document-flow/document-flow-root';
 import { ShowFieldItem } from '../document-flow/show-field-item';
@@ -168,6 +169,10 @@ export const AddTemplatePlaceholderRecipientsFormPartial = ({
 
   return (
     <>
+      <DocumentFlowFormContainerHeader
+        title={documentFlow.title}
+        description={documentFlow.description}
+      />
       <DocumentFlowFormContainerContent>
         {isDocumentPdfLoaded &&
           fields.map((field, index) => (
diff --git a/packages/ui/primitives/template-flow/add-template-settings.tsx b/packages/ui/primitives/template-flow/add-template-settings.tsx
index 2d108f08d..413f48b5f 100644
--- a/packages/ui/primitives/template-flow/add-template-settings.tsx
+++ b/packages/ui/primitives/template-flow/add-template-settings.tsx
@@ -40,6 +40,7 @@ import {
   DocumentFlowFormContainerActions,
   DocumentFlowFormContainerContent,
   DocumentFlowFormContainerFooter,
+  DocumentFlowFormContainerHeader,
   DocumentFlowFormContainerStep,
 } from '../document-flow/document-flow-root';
 import { ShowFieldItem } from '../document-flow/show-field-item';
@@ -104,6 +105,11 @@ export const AddTemplateSettingsFormPartial = ({
 
   return (
     <>
+      <DocumentFlowFormContainerHeader
+        title={documentFlow.title}
+        description={documentFlow.description}
+      />
+
       <DocumentFlowFormContainerContent>
         {isDocumentPdfLoaded &&
           fields.map((field, index) => (
diff --git a/packages/ui/styles/theme.css b/packages/ui/styles/theme.css
index 0b5bc587f..0a8b65ae1 100644
--- a/packages/ui/styles/theme.css
+++ b/packages/ui/styles/theme.css
@@ -46,6 +46,13 @@
     --warning: 54 96% 45%;
 
     --gold: 47.9 95.8% 53.1%;
+
+    --signer-green: 100 48% 55%;
+    --signer-blue: 212 56% 50%;
+    --signer-purple: 266 100% 64%;
+    --signer-orange: 36 92% 54%;
+    --signer-yellow: 51 100% 43%;
+    --signer-pink: 313 65% 57%;
   }
 
   .dark {
diff --git a/packages/ui/tsconfig.json b/packages/ui/tsconfig.json
index 32900f755..78beb0a91 100644
--- a/packages/ui/tsconfig.json
+++ b/packages/ui/tsconfig.json
@@ -1,11 +1,11 @@
 {
   "extends": "@documenso/tsconfig/react-library.json",
-  "compilerOptions": {
-    "baseUrl": ".",
-    "paths": {
-      "@/*": ["./*"]
-    }
-  },
-  "include": ["."],
-  "exclude": ["dist", "build", "node_modules"]
-}
+  "include": [
+    "."
+  ],
+  "exclude": [
+    "dist",
+    "build",
+    "node_modules"
+  ]
+}
\ No newline at end of file
diff --git a/turbo.json b/turbo.json
index c09715c45..3d7ce4059 100644
--- a/turbo.json
+++ b/turbo.json
@@ -12,12 +12,9 @@
       ]
     },
     "prebuild": {
+      "cache": false,
       "dependsOn": [
         "^prebuild"
-      ],
-      "outputs": [
-        ".next/**",
-        "!.next/cache/**"
       ]
     },
     "lint": {
@@ -141,4 +138,4 @@
     "E2E_TEST_AUTHENTICATE_USER_EMAIL",
     "E2E_TEST_AUTHENTICATE_USER_PASSWORD"
   ]
-}
\ No newline at end of file
+}