diff --git a/.devcontainer/devcontainer.json b/.devcontainer/devcontainer.json
index 60b385403..3471f4f88 100644
--- a/.devcontainer/devcontainer.json
+++ b/.devcontainer/devcontainer.json
@@ -10,7 +10,13 @@
     "ghcr.io/devcontainers/features/node:1": {}
   },
   "onCreateCommand": "./.devcontainer/on-create.sh",
-  "forwardPorts": [3000, 54320, 9000, 2500, 1100],
+  "forwardPorts": [
+    3000,
+    54320,
+    9000,
+    2500,
+    1100
+  ],
   "customizations": {
     "vscode": {
       "extensions": [
@@ -25,8 +31,8 @@
         "GitHub.copilot",
         "GitHub.vscode-pull-request-github",
         "Prisma.prisma",
-        "VisualStudioExptTeam.vscodeintellicode",
+        "VisualStudioExptTeam.vscodeintellicode"
       ]
     }
   }
-}
+}
\ No newline at end of file
diff --git a/apps/web/src/app/(dashboard)/settings/profile/delete-account-dialog.tsx b/apps/web/src/app/(dashboard)/settings/profile/delete-account-dialog.tsx
new file mode 100644
index 000000000..933b37f31
--- /dev/null
+++ b/apps/web/src/app/(dashboard)/settings/profile/delete-account-dialog.tsx
@@ -0,0 +1,124 @@
+'use client';
+
+import { signOut } from 'next-auth/react';
+
+import type { User } from '@documenso/prisma/client';
+import { TRPCClientError } from '@documenso/trpc/client';
+import { trpc } from '@documenso/trpc/react';
+import { Alert, AlertDescription, AlertTitle } from '@documenso/ui/primitives/alert';
+import { Button } from '@documenso/ui/primitives/button';
+import {
+  Dialog,
+  DialogContent,
+  DialogDescription,
+  DialogFooter,
+  DialogHeader,
+  DialogTitle,
+  DialogTrigger,
+} from '@documenso/ui/primitives/dialog';
+import { useToast } from '@documenso/ui/primitives/use-toast';
+
+export type DeleteAccountDialogProps = {
+  className?: string;
+  user: User;
+};
+
+export const DeleteAccountDialog = ({ className, user }: DeleteAccountDialogProps) => {
+  const { toast } = useToast();
+
+  const hasTwoFactorAuthentication = user.twoFactorEnabled;
+
+  const { mutateAsync: deleteAccount, isLoading: isDeletingAccount } =
+    trpc.profile.deleteAccount.useMutation();
+
+  const onDeleteAccount = async () => {
+    try {
+      await deleteAccount();
+
+      toast({
+        title: 'Account deleted',
+        description: 'Your account has been deleted successfully.',
+        duration: 5000,
+      });
+
+      return await signOut({ callbackUrl: '/' });
+    } catch (err) {
+      if (err instanceof TRPCClientError && err.data?.code === 'BAD_REQUEST') {
+        toast({
+          title: 'An error occurred',
+          description: err.message,
+          variant: 'destructive',
+        });
+      } else {
+        toast({
+          title: 'An unknown error occurred',
+          variant: 'destructive',
+          description:
+            err.message ??
+            'We encountered an unknown error while attempting to delete your account. Please try again later.',
+        });
+      }
+    }
+  };
+
+  return (
+    <div className={className}>
+      <Alert
+        className="flex flex-col items-center justify-between gap-4 p-6 md:flex-row "
+        variant="neutral"
+      >
+        <div>
+          <AlertTitle>Delete Account</AlertTitle>
+          <AlertDescription className="mr-2">
+            Delete your account and all its contents, including completed documents. This action is
+            irreversible and will cancel your subscription, so proceed with caution.
+          </AlertDescription>
+        </div>
+
+        <div className="flex-shrink-0">
+          <Dialog>
+            <DialogTrigger asChild>
+              <Button variant="destructive">Delete Account</Button>
+            </DialogTrigger>
+            <DialogContent>
+              <DialogHeader className="space-y-4">
+                <DialogTitle>Delete Account</DialogTitle>
+
+                <Alert variant="destructive">
+                  <AlertDescription className="selection:bg-red-100">
+                    This action is not reversible. Please be certain.
+                  </AlertDescription>
+                </Alert>
+
+                {hasTwoFactorAuthentication && (
+                  <Alert variant="destructive">
+                    <AlertDescription className="selection:bg-red-100">
+                      Disable Two Factor Authentication before deleting your account.
+                    </AlertDescription>
+                  </Alert>
+                )}
+
+                <DialogDescription>
+                  Documenso will delete <span className="font-semibold">all of your documents</span>
+                  , along with all of your completed documents, signatures, and all other resources
+                  belonging to your Account.
+                </DialogDescription>
+              </DialogHeader>
+
+              <DialogFooter>
+                <Button
+                  onClick={onDeleteAccount}
+                  loading={isDeletingAccount}
+                  variant="destructive"
+                  disabled={hasTwoFactorAuthentication}
+                >
+                  {isDeletingAccount ? 'Deleting account...' : 'Delete Account'}
+                </Button>
+              </DialogFooter>
+            </DialogContent>
+          </Dialog>
+        </div>
+      </Alert>
+    </div>
+  );
+};
diff --git a/apps/web/src/app/(dashboard)/settings/profile/page.tsx b/apps/web/src/app/(dashboard)/settings/profile/page.tsx
index 2890eb5d5..11cfc8515 100644
--- a/apps/web/src/app/(dashboard)/settings/profile/page.tsx
+++ b/apps/web/src/app/(dashboard)/settings/profile/page.tsx
@@ -5,6 +5,8 @@ import { getRequiredServerComponentSession } from '@documenso/lib/next-auth/get-
 import { SettingsHeader } from '~/components/(dashboard)/settings/layout/header';
 import { ProfileForm } from '~/components/forms/profile';
 
+import { DeleteAccountDialog } from './delete-account-dialog';
+
 export const metadata: Metadata = {
   title: 'Profile',
 };
@@ -16,7 +18,9 @@ export default async function ProfileSettingsPage() {
     <div>
       <SettingsHeader title="Profile" subtitle="Here you can edit your personal details." />
 
-      <ProfileForm user={user} className="max-w-xl" />
+      <ProfileForm className="max-w-xl" user={user} />
+
+      <DeleteAccountDialog className="mt-8 max-w-xl" user={user} />
     </div>
   );
 }
diff --git a/apps/web/src/components/forms/profile.tsx b/apps/web/src/components/forms/profile.tsx
index 2c278292f..c3f8eca37 100644
--- a/apps/web/src/components/forms/profile.tsx
+++ b/apps/web/src/components/forms/profile.tsx
@@ -29,6 +29,11 @@ export const ZProfileFormSchema = z.object({
   signature: z.string().min(1, 'Signature Pad cannot be empty'),
 });
 
+export const ZTwoFactorAuthTokenSchema = z.object({
+  token: z.string(),
+});
+
+export type TTwoFactorAuthTokenSchema = z.infer<typeof ZTwoFactorAuthTokenSchema>;
 export type TProfileFormSchema = z.infer<typeof ZProfileFormSchema>;
 
 export type ProfileFormProps = {
@@ -50,8 +55,11 @@ export const ProfileForm = ({ className, user }: ProfileFormProps) => {
   });
 
   const isSubmitting = form.formState.isSubmitting;
+  const hasTwoFactorAuthentication = user.twoFactorEnabled;
 
   const { mutateAsync: updateProfile } = trpc.profile.updateProfile.useMutation();
+  const { mutateAsync: deleteAccount, isLoading: isDeletingAccount } =
+    trpc.profile.deleteAccount.useMutation();
 
   const onFormSubmit = async ({ name, signature }: TProfileFormSchema) => {
     try {
@@ -133,7 +141,7 @@ export const ProfileForm = ({ className, user }: ProfileFormProps) => {
           />
         </fieldset>
 
-        <Button type="submit" loading={isSubmitting}>
+        <Button type="submit" loading={isSubmitting} className="self-end">
           {isSubmitting ? 'Updating profile...' : 'Update profile'}
         </Button>
       </form>
diff --git a/packages/lib/server-only/2fa/validate-2fa.ts b/packages/lib/server-only/2fa/validate-2fa.ts
index 7fc76a8bb..33141c325 100644
--- a/packages/lib/server-only/2fa/validate-2fa.ts
+++ b/packages/lib/server-only/2fa/validate-2fa.ts
@@ -1,4 +1,4 @@
-import { User } from '@documenso/prisma/client';
+import type { User } from '@documenso/prisma/client';
 
 import { ErrorCode } from '../../next-auth/error-codes';
 import { verifyTwoFactorAuthenticationToken } from './verify-2fa-token';
diff --git a/packages/lib/server-only/2fa/verify-2fa-token.ts b/packages/lib/server-only/2fa/verify-2fa-token.ts
index fa9159517..0e8ec6afc 100644
--- a/packages/lib/server-only/2fa/verify-2fa-token.ts
+++ b/packages/lib/server-only/2fa/verify-2fa-token.ts
@@ -1,7 +1,7 @@
 import { base32 } from '@scure/base';
 import { TOTPController } from 'oslo/otp';
 
-import { User } from '@documenso/prisma/client';
+import type { User } from '@documenso/prisma/client';
 
 import { DOCUMENSO_ENCRYPTION_KEY } from '../../constants/crypto';
 import { symmetricDecrypt } from '../../universal/crypto';
diff --git a/packages/lib/server-only/user/delete-user.ts b/packages/lib/server-only/user/delete-user.ts
index df5132aff..d6d4284b4 100644
--- a/packages/lib/server-only/user/delete-user.ts
+++ b/packages/lib/server-only/user/delete-user.ts
@@ -1,4 +1,7 @@
 import { prisma } from '@documenso/prisma';
+import { DocumentStatus } from '@documenso/prisma/client';
+
+import { deletedAccountServiceAccount } from './service-accounts/deleted-account';
 
 export type DeleteUserOptions = {
   email: string;
@@ -17,6 +20,22 @@ export const deleteUser = async ({ email }: DeleteUserOptions) => {
     throw new Error(`User with email ${email} not found`);
   }
 
+  const serviceAccount = await deletedAccountServiceAccount();
+
+  // TODO: Send out cancellations for all pending docs
+  await prisma.document.updateMany({
+    where: {
+      userId: user.id,
+      status: {
+        in: [DocumentStatus.PENDING, DocumentStatus.COMPLETED],
+      },
+    },
+    data: {
+      userId: serviceAccount.id,
+      deletedAt: new Date(),
+    },
+  });
+
   return await prisma.user.delete({
     where: {
       id: user.id,
diff --git a/packages/lib/server-only/user/service-accounts/deleted-account.ts b/packages/lib/server-only/user/service-accounts/deleted-account.ts
new file mode 100644
index 000000000..6bfd6d25f
--- /dev/null
+++ b/packages/lib/server-only/user/service-accounts/deleted-account.ts
@@ -0,0 +1,17 @@
+import { prisma } from '@documenso/prisma';
+
+export const deletedAccountServiceAccount = async () => {
+  const serviceAccount = await prisma.user.findFirst({
+    where: {
+      email: 'deleted-account@documenso.com',
+    },
+  });
+
+  if (!serviceAccount) {
+    throw new Error(
+      'Deleted account service account not found, have you ran the appropriate migrations?',
+    );
+  }
+
+  return serviceAccount;
+};
diff --git a/packages/prisma/migrations/20240205120648_create_delete_account/migration.sql b/packages/prisma/migrations/20240205120648_create_delete_account/migration.sql
new file mode 100644
index 000000000..d001bc4ae
--- /dev/null
+++ b/packages/prisma/migrations/20240205120648_create_delete_account/migration.sql
@@ -0,0 +1,30 @@
+-- Create deleted@documenso.com
+DO $$
+BEGIN  
+  IF NOT EXISTS (SELECT 1 FROM "public"."User" WHERE "email" = 'deleted-account@documenso.com') THEN  
+    INSERT INTO
+      "public"."User" (
+        "email",
+        "emailVerified",
+        "password",
+        "createdAt",
+        "updatedAt",
+        "lastSignedIn",
+        "roles",
+        "identityProvider",
+        "twoFactorEnabled"
+      )
+    VALUES
+      (
+        'deleted-account@documenso.com',
+        NOW(),
+        NULL,
+        NOW(),
+        NOW(),
+        NOW(),
+        ARRAY['USER'::TEXT]::"public"."Role" [],
+        CAST('GOOGLE'::TEXT AS "public"."IdentityProvider"),
+        FALSE
+      );
+  END IF;  
+END $$
diff --git a/packages/trpc/react/index.tsx b/packages/trpc/react/index.tsx
index 85161d0e8..ce80ba267 100644
--- a/packages/trpc/react/index.tsx
+++ b/packages/trpc/react/index.tsx
@@ -9,7 +9,7 @@ import SuperJSON from 'superjson';
 
 import { getBaseUrl } from '@documenso/lib/universal/get-base-url';
 
-import { AppRouter } from '../server/router';
+import type { AppRouter } from '../server/router';
 
 export const trpc = createTRPCReact<AppRouter>({
   unstable_overrides: {
diff --git a/packages/trpc/server/profile-router/router.ts b/packages/trpc/server/profile-router/router.ts
index bceee020a..2f636d87d 100644
--- a/packages/trpc/server/profile-router/router.ts
+++ b/packages/trpc/server/profile-router/router.ts
@@ -1,5 +1,6 @@
 import { TRPCError } from '@trpc/server';
 
+import { deleteUser } from '@documenso/lib/server-only/user/delete-user';
 import { findUserSecurityAuditLogs } from '@documenso/lib/server-only/user/find-user-security-audit-logs';
 import { forgotPassword } from '@documenso/lib/server-only/user/forgot-password';
 import { getUserById } from '@documenso/lib/server-only/user/get-user-by-id';
@@ -155,4 +156,23 @@ export const profileRouter = router({
         });
       }
     }),
+
+  deleteAccount: authenticatedProcedure.mutation(async ({ ctx }) => {
+    try {
+      const user = ctx.user;
+
+      return await deleteUser(user);
+    } catch (err) {
+      let message = 'We were unable to delete your account. Please try again.';
+
+      if (err instanceof Error) {
+        message = err.message;
+      }
+
+      throw new TRPCError({
+        code: 'BAD_REQUEST',
+        message,
+      });
+    }
+  }),
 });
diff --git a/packages/ui/primitives/button.tsx b/packages/ui/primitives/button.tsx
index 5fc3fc1bb..add486332 100644
--- a/packages/ui/primitives/button.tsx
+++ b/packages/ui/primitives/button.tsx
@@ -13,7 +13,8 @@ const buttonVariants = cva(
     variants: {
       variant: {
         default: 'bg-primary text-primary-foreground hover:bg-primary/90',
-        destructive: 'bg-destructive text-destructive-foreground hover:bg-destructive/90',
+        destructive:
+          'bg-destructive text-destructive-foreground hover:bg-destructive/90 focus-visible:ring-destructive',
         outline: 'border border-input hover:bg-accent hover:text-accent-foreground',
         secondary: 'bg-secondary text-secondary-foreground hover:bg-secondary/80',
         ghost: 'hover:bg-accent hover:text-accent-foreground',