Merge branch 'main' into feat/add-attachments-reworked

packages/api/v1/schema.ts

@@ -310,12 +310,11 @@ export const ZGenerateDocumentFromTemplateMutationSchema = z.object({
     )
     .refine(
       (schema) => {
-        const emails = schema.map((signer) => signer.email.toLowerCase());
         const ids = schema.map((signer) => signer.id);
 
-        return new Set(emails).size === emails.length && new Set(ids).size === ids.length;
+        return new Set(ids).size === ids.length;
       },
-      { message: 'Recipient IDs and emails must be unique' },
+      { message: 'Recipient IDs must be unique' },
     ),
   meta: z
     .object({

packages/app-tests/e2e/admin/organisations/promote-member-to-owner.spec.ts

@@ -0,0 +1,435 @@
+import { expect, test } from '@playwright/test';
+
+import { nanoid } from '@documenso/lib/universal/id';
+import { seedOrganisationMembers } from '@documenso/prisma/seed/organisations';
+import { seedUser } from '@documenso/prisma/seed/users';
+
+import { apiSignin } from '../../fixtures/authentication';
+
+test('[ADMIN]: promote member to owner', async ({ page }) => {
+  // Create an admin user who can access the admin panel
+  const { user: adminUser } = await seedUser({
+    isAdmin: true,
+  });
+
+  // Create an organisation owner
+  const { user: ownerUser, organisation } = await seedUser({
+    isPersonalOrganisation: false,
+  });
+
+  // Create organisation members with different roles
+  const memberEmail = `member-${nanoid()}@test.documenso.com`;
+  const managerEmail = `manager-${nanoid()}@test.documenso.com`;
+  const adminMemberEmail = `admin-member-${nanoid()}@test.documenso.com`;
+
+  const [memberUser, managerUser, adminMemberUser] = await seedOrganisationMembers({
+    members: [
+      {
+        email: memberEmail,
+        name: 'Test Member',
+        organisationRole: 'MEMBER',
+      },
+      {
+        email: managerEmail,
+        name: 'Test Manager',
+        organisationRole: 'MANAGER',
+      },
+      {
+        email: adminMemberEmail,
+        name: 'Test Admin Member',
+        organisationRole: 'ADMIN',
+      },
+    ],
+    organisationId: organisation.id,
+  });
+
+  // Sign in as admin and navigate to the organisation admin page
+  await apiSignin({
+    page,
+    email: adminUser.email,
+    redirectPath: `/admin/organisations/${organisation.id}`,
+  });
+
+  // Verify we're on the admin organisation page
+  await expect(page.getByText(`Manage organisation`)).toBeVisible();
+
+  await expect(page.getByLabel('Organisation Name')).toHaveValue(organisation.name);
+
+  // Check that the organisation members table shows the correct roles
+  const ownerRow = page.getByRole('row', { name: ownerUser.email });
+
+  await expect(ownerRow).toBeVisible();
+  await expect(ownerRow.getByRole('status').filter({ hasText: 'Owner' })).toBeVisible();
+
+  await expect(page.getByRole('row', { name: memberUser.email })).toBeVisible();
+  await expect(page.getByRole('row', { name: adminMemberUser.email })).toBeVisible();
+  await expect(page.getByRole('row', { name: managerUser.email })).toBeVisible();
+
+  // Test promoting a MEMBER to owner
+  const memberRow = page.getByRole('row', { name: memberUser.email });
+
+  // Find and click the "Promote to owner" button for the member
+  const promoteButton = memberRow.getByRole('button', { name: 'Promote to owner' });
+  await expect(promoteButton).toBeVisible();
+  await expect(promoteButton).not.toBeDisabled();
+
+  await promoteButton.click();
+
+  // Verify success toast appears
+  await expect(page.getByText('Member promoted to owner successfully').first()).toBeVisible();
+
+  // Reload the page to see the changes
+  await page.reload();
+
+  // Verify that the member is now the owner
+  const newOwnerRow = page.getByRole('row', { name: memberUser.email });
+  await expect(newOwnerRow.getByRole('status').filter({ hasText: 'Owner' })).toBeVisible();
+
+  // Verify that the previous owner is no longer marked as owner
+  const previousOwnerRow = page.getByRole('row', { name: ownerUser.email });
+  await expect(previousOwnerRow.getByRole('status').filter({ hasText: 'Owner' })).not.toBeVisible();
+
+  // Verify that the promote button is now disabled for the new owner
+  const newOwnerPromoteButton = newOwnerRow.getByRole('button', { name: 'Promote to owner' });
+  await expect(newOwnerPromoteButton).toBeDisabled();
+
+  // Test that we can't promote the current owner (button should be disabled)
+  await expect(newOwnerPromoteButton).toHaveAttribute('disabled');
+});
+
+test('[ADMIN]: promote manager to owner', async ({ page }) => {
+  // Create an admin user who can access the admin panel
+  const { user: adminUser } = await seedUser({
+    isAdmin: true,
+  });
+
+  // Create an organisation with owner and manager
+  const { organisation } = await seedUser({
+    isPersonalOrganisation: false,
+  });
+
+  const managerEmail = `manager-${nanoid()}@test.documenso.com`;
+
+  const [managerUser] = await seedOrganisationMembers({
+    members: [
+      {
+        email: managerEmail,
+        name: 'Test Manager',
+        organisationRole: 'MANAGER',
+      },
+    ],
+    organisationId: organisation.id,
+  });
+
+  // Sign in as admin
+  await apiSignin({
+    page,
+    email: adminUser.email,
+    redirectPath: `/admin/organisations/${organisation.id}`,
+  });
+
+  // Promote the manager to owner
+  const managerRow = page.getByRole('row', { name: managerUser.email });
+  const promoteButton = managerRow.getByRole('button', { name: 'Promote to owner' });
+
+  await promoteButton.click();
+  await expect(page.getByText('Member promoted to owner successfully').first()).toBeVisible();
+
+  // Reload and verify the change
+  await page.reload();
+  await expect(managerRow.getByRole('status').filter({ hasText: 'Owner' })).toBeVisible();
+});
+
+test('[ADMIN]: promote admin member to owner', async ({ page }) => {
+  // Create an admin user who can access the admin panel
+  const { user: adminUser } = await seedUser({
+    isAdmin: true,
+  });
+
+  // Create an organisation with owner and admin member
+  const { organisation } = await seedUser({
+    isPersonalOrganisation: false,
+  });
+
+  const adminMemberEmail = `admin-member-${nanoid()}@test.documenso.com`;
+
+  const [adminMemberUser] = await seedOrganisationMembers({
+    members: [
+      {
+        email: adminMemberEmail,
+        name: 'Test Admin Member',
+        organisationRole: 'ADMIN',
+      },
+    ],
+    organisationId: organisation.id,
+  });
+
+  // Sign in as admin
+  await apiSignin({
+    page,
+    email: adminUser.email,
+    redirectPath: `/admin/organisations/${organisation.id}`,
+  });
+
+  // Promote the admin member to owner
+  const adminMemberRow = page.getByRole('row', { name: adminMemberUser.email });
+  const promoteButton = adminMemberRow.getByRole('button', { name: 'Promote to owner' });
+
+  await promoteButton.click();
+
+  await expect(page.getByText('Member promoted to owner successfully').first()).toBeVisible({
+    timeout: 10_000,
+  });
+
+  // Reload and verify the change
+  await page.reload();
+  await expect(adminMemberRow.getByRole('status').filter({ hasText: 'Owner' })).toBeVisible();
+});
+
+test('[ADMIN]: cannot promote non-existent user', async ({ page }) => {
+  // Create an admin user
+  const { user: adminUser } = await seedUser({
+    isAdmin: true,
+  });
+
+  // Create an organisation
+  const { organisation } = await seedUser({
+    isPersonalOrganisation: false,
+  });
+
+  // Sign in as admin
+  await apiSignin({
+    page,
+    email: adminUser.email,
+    redirectPath: `/admin/organisations/${organisation.id}`,
+  });
+
+  // Try to manually call the API with invalid data - this should be handled by the UI validation
+  // In a real scenario, the promote button wouldn't be available for non-existent users
+  // But we can test that the API properly handles invalid requests
+
+  // For now, just verify that non-existent users don't show up in the members table
+  await expect(page.getByRole('row', { name: 'Non Existent User' })).not.toBeVisible();
+});
+
+test('[ADMIN]: verify role hierarchy after promotion', async ({ page }) => {
+  // Create an admin user
+  const { user: adminUser } = await seedUser({
+    isAdmin: true,
+  });
+
+  // Create organisation with a member
+  const { organisation } = await seedUser({
+    isPersonalOrganisation: false,
+  });
+
+  const memberEmail = `member-${nanoid()}@test.documenso.com`;
+
+  const [memberUser] = await seedOrganisationMembers({
+    members: [
+      {
+        email: memberEmail,
+        name: 'Test Member',
+        organisationRole: 'MEMBER',
+      },
+    ],
+    organisationId: organisation.id,
+  });
+
+  // Sign in as admin
+  await apiSignin({
+    page,
+    email: adminUser.email,
+    redirectPath: `/admin/organisations/${organisation.id}`,
+  });
+
+  // Before promotion - verify member has MEMBER role
+  let memberRow = page.getByRole('row', { name: memberUser.email });
+  await expect(memberRow).toBeVisible();
+  await expect(memberRow.getByRole('status').filter({ hasText: 'Owner' })).not.toBeVisible();
+
+  // Promote member to owner
+  const promoteButton = memberRow.getByRole('button', { name: 'Promote to owner' });
+  await promoteButton.click();
+  await expect(page.getByText('Member promoted to owner successfully').first()).toBeVisible({
+    timeout: 10_000,
+  });
+
+  // Reload page to see updated state
+  await page.reload();
+
+  // After promotion - verify member is now owner and has admin permissions
+  memberRow = page.getByRole('row', { name: memberUser.email });
+  await expect(memberRow.getByRole('status').filter({ hasText: 'Owner' })).toBeVisible();
+
+  // Verify the promote button is now disabled for the new owner
+  const newOwnerPromoteButton = memberRow.getByRole('button', { name: 'Promote to owner' });
+  await expect(newOwnerPromoteButton).toBeDisabled();
+
+  // Sign in as the newly promoted user to verify they have owner permissions
+  await apiSignin({
+    page,
+    email: memberUser.email,
+    redirectPath: `/o/${organisation.url}/settings/general`,
+  });
+
+  // Verify they can access organisation settings (owner permission)
+  await expect(page.getByText('Organisation Settings')).toBeVisible();
+  await expect(page.getByRole('button', { name: 'Delete' })).toBeVisible();
+});
+
+test('[ADMIN]: error handling for invalid organisation', async ({ page }) => {
+  // Create an admin user
+  const { user: adminUser } = await seedUser({
+    isAdmin: true,
+  });
+
+  // Sign in as admin and try to access non-existent organisation
+  await apiSignin({
+    page,
+    email: adminUser.email,
+    redirectPath: `/admin/organisations/non-existent-org-id`,
+  });
+
+  // Should show 404 error
+  await expect(page.getByRole('heading', { name: 'Organisation not found' })).toBeVisible({
+    timeout: 10_000,
+  });
+});
+
+test('[ADMIN]: multiple promotions in sequence', async ({ page }) => {
+  // Create an admin user
+  const { user: adminUser } = await seedUser({
+    isAdmin: true,
+  });
+
+  // Create organisation with multiple members
+  const { organisation } = await seedUser({
+    isPersonalOrganisation: false,
+  });
+
+  const member1Email = `member1-${nanoid()}@test.documenso.com`;
+  const member2Email = `member2-${nanoid()}@test.documenso.com`;
+
+  const [member1User, member2User] = await seedOrganisationMembers({
+    members: [
+      {
+        email: member1Email,
+        name: 'Test Member 1',
+        organisationRole: 'MEMBER',
+      },
+      {
+        email: member2Email,
+        name: 'Test Member 2',
+        organisationRole: 'MANAGER',
+      },
+    ],
+    organisationId: organisation.id,
+  });
+
+  // Sign in as admin
+  await apiSignin({
+    page,
+    email: adminUser.email,
+    redirectPath: `/admin/organisations/${organisation.id}`,
+  });
+
+  // First promotion: Member 1 becomes owner
+  let member1Row = page.getByRole('row', { name: member1User.email });
+  let promoteButton1 = member1Row.getByRole('button', { name: 'Promote to owner' });
+  await promoteButton1.click();
+  await expect(page.getByText('Member promoted to owner successfully').first()).toBeVisible({
+    timeout: 10_000,
+  });
+
+  await page.reload();
+
+  // Verify Member 1 is now owner and button is disabled
+  member1Row = page.getByRole('row', { name: member1User.email });
+  await expect(member1Row.getByRole('status').filter({ hasText: 'Owner' })).toBeVisible();
+  promoteButton1 = member1Row.getByRole('button', { name: 'Promote to owner' });
+  await expect(promoteButton1).toBeDisabled();
+
+  // Second promotion: Member 2 becomes the new owner
+  const member2Row = page.getByRole('row', { name: member2User.email });
+  const promoteButton2 = member2Row.getByRole('button', { name: 'Promote to owner' });
+  await expect(promoteButton2).not.toBeDisabled();
+  await promoteButton2.click();
+  await expect(page.getByText('Member promoted to owner successfully').first()).toBeVisible({
+    timeout: 10_000,
+  });
+
+  await page.reload();
+
+  // Verify Member 2 is now owner and Member 1 is no longer owner
+  await expect(member2Row.getByRole('status').filter({ hasText: 'Owner' })).toBeVisible();
+  await expect(member1Row.getByRole('status').filter({ hasText: 'Owner' })).not.toBeVisible();
+
+  // Verify Member 1's promote button is now enabled again
+  const newPromoteButton1 = member1Row.getByRole('button', { name: 'Promote to owner' });
+  await expect(newPromoteButton1).not.toBeDisabled();
+});
+
+test('[ADMIN]: verify organisation access after ownership change', async ({ page }) => {
+  // Create admin user
+  const { user: adminUser } = await seedUser({
+    isAdmin: true,
+  });
+
+  // Create organisation with owner and member
+  const { user: originalOwner, organisation } = await seedUser({
+    isPersonalOrganisation: false,
+  });
+
+  const memberEmail = `member-${nanoid()}@test.documenso.com`;
+
+  const [memberUser] = await seedOrganisationMembers({
+    members: [
+      {
+        email: memberEmail,
+        name: 'Test Member',
+        organisationRole: 'MEMBER',
+      },
+    ],
+    organisationId: organisation.id,
+  });
+
+  // Sign in as admin and promote member to owner
+  await apiSignin({
+    page,
+    email: adminUser.email,
+    redirectPath: `/admin/organisations/${organisation.id}`,
+  });
+
+  const memberRow = page.getByRole('row', { name: memberUser.email });
+  const promoteButton = memberRow.getByRole('button', { name: 'Promote to owner' });
+  await promoteButton.click();
+  await expect(page.getByText('Member promoted to owner successfully').first()).toBeVisible({
+    timeout: 10_000,
+  });
+
+  // Test that the new owner can access organisation settings
+  await apiSignin({
+    page,
+    email: memberUser.email,
+    redirectPath: `/o/${organisation.url}/settings/general`,
+  });
+
+  // Should be able to access organisation settings
+  await expect(page.getByText('Organisation Settings')).toBeVisible();
+  await expect(page.getByLabel('Organisation Name*')).toBeVisible();
+  await expect(page.getByRole('button', { name: 'Update organisation' })).toBeVisible();
+
+  // Should have delete permissions
+  await expect(page.getByRole('button', { name: 'Delete' })).toBeVisible();
+
+  // Test that the original owner no longer has owner-level access
+  await apiSignin({
+    page,
+    email: originalOwner.email,
+    redirectPath: `/o/${organisation.url}/settings/general`,
+  });
+
+  // Should still be able to access settings (as they should now be an admin)
+  await expect(page.getByText('Organisation Settings')).toBeVisible();
+});

packages/app-tests/e2e/document-flow/autosave-fields-step.spec.ts

@@ -33,7 +33,7 @@ const setupDocumentAndNavigateToFieldsStep = async (page: Page) => {
 };
 
 const triggerAutosave = async (page: Page) => {
-  await page.locator('#document-flow-form-container').click();
+  await page.locator('body').click({ position: { x: 0, y: 0 } });
   await page.locator('#document-flow-form-container').blur();
 
   await page.waitForTimeout(5000);
@@ -70,7 +70,7 @@ test.describe('AutoSave Fields Step', () => {
 
     await triggerAutosave(page);
 
-    await page.getByRole('combobox').click();
+    await page.getByRole('combobox').first().click();
     await page.getByRole('option', { name: 'Recipient 2 (recipient2@documenso.com)' }).click();
 
     await page.getByRole('button', { name: 'Signature' }).click();
@@ -127,7 +127,7 @@ test.describe('AutoSave Fields Step', () => {
 
     await triggerAutosave(page);
 
-    await page.getByRole('combobox').click();
+    await page.getByRole('combobox').first().click();
     await page.getByRole('option', { name: 'Recipient 2 (recipient2@documenso.com)' }).click();
 
     await page.getByRole('button', { name: 'Signature' }).click();
@@ -140,7 +140,7 @@ test.describe('AutoSave Fields Step', () => {
 
     await triggerAutosave(page);
 
-    await page.getByRole('combobox').click();
+    await page.getByRole('combobox').first().click();
     await page.getByRole('option', { name: 'Recipient 1 (recipient1@documenso.com)' }).click();
 
     await page.getByText('Text').nth(1).click();
@@ -191,7 +191,7 @@ test.describe('AutoSave Fields Step', () => {
 
     await triggerAutosave(page);
 
-    await page.getByRole('combobox').click();
+    await page.getByRole('combobox').first().click();
     await page.getByRole('option', { name: 'Recipient 2 (recipient2@documenso.com)' }).click();
 
     await page.getByRole('button', { name: 'Signature' }).click();
@@ -204,7 +204,7 @@ test.describe('AutoSave Fields Step', () => {
 
     await triggerAutosave(page);
 
-    await page.getByRole('combobox').click();
+    await page.getByRole('combobox').first().click();
     await page.getByRole('option', { name: 'Recipient 1 (recipient1@documenso.com)' }).click();
 
     await page.getByText('Signature').nth(1).click();

packages/app-tests/e2e/document-flow/autosave-settings-step.spec.ts

@@ -24,7 +24,7 @@ const setupDocument = async (page: Page) => {
 };
 
 const triggerAutosave = async (page: Page) => {
-  await page.locator('#document-flow-form-container').click();
+  await page.locator('body').click({ position: { x: 0, y: 0 } });
   await page.locator('#document-flow-form-container').blur();
 
   await page.waitForTimeout(5000);

packages/app-tests/e2e/document-flow/autosave-signers-step.spec.ts

@@ -26,7 +26,7 @@ const setupDocumentAndNavigateToSignersStep = async (page: Page) => {
 };
 
 const triggerAutosave = async (page: Page) => {
-  await page.locator('#document-flow-form-container').click();
+  await page.locator('body').click({ position: { x: 0, y: 0 } });
   await page.locator('#document-flow-form-container').blur();
 
   await page.waitForTimeout(5000);
@@ -92,7 +92,7 @@ test.describe('AutoSave Signers Step', () => {
 
     await triggerAutosave(page);
 
-    await page.getByRole('combobox').click();
+    await page.getByRole('combobox').first().click();
     await page.getByRole('option', { name: 'Receives copy' }).click();
 
     await triggerAutosave(page);
@@ -160,9 +160,20 @@ test.describe('AutoSave Signers Step', () => {
       expect(retrievedDocumentData.documentMeta?.signingOrder).toBe('SEQUENTIAL');
       expect(retrievedDocumentData.documentMeta?.allowDictateNextSigner).toBe(true);
       expect(retrievedRecipients.length).toBe(3);
-      expect(retrievedRecipients[0].signingOrder).toBe(2);
-      expect(retrievedRecipients[1].signingOrder).toBe(3);
-      expect(retrievedRecipients[2].signingOrder).toBe(1);
+
+      const firstRecipient = retrievedRecipients.find(
+        (r) => r.email === 'recipient1@documenso.com',
+      );
+      const secondRecipient = retrievedRecipients.find(
+        (r) => r.email === 'recipient2@documenso.com',
+      );
+      const thirdRecipient = retrievedRecipients.find(
+        (r) => r.email === 'recipient3@documenso.com',
+      );
+
+      expect(firstRecipient?.signingOrder).toBe(2);
+      expect(secondRecipient?.signingOrder).toBe(3);
+      expect(thirdRecipient?.signingOrder).toBe(1);
     }).toPass();
   });
 });

packages/app-tests/e2e/document-flow/autosave-subject-step.spec.ts

@@ -42,7 +42,7 @@ export const setupDocumentAndNavigateToSubjectStep = async (page: Page) => {
 };
 
 export const triggerAutosave = async (page: Page) => {
-  await page.locator('#document-flow-form-container').click();
+  await page.locator('body').click({ position: { x: 0, y: 0 } });
   await page.locator('#document-flow-form-container').blur();
 
   await page.waitForTimeout(5000);

packages/app-tests/e2e/document-flow/duplicate-recipients-simple.spec.ts

@@ -0,0 +1,56 @@
+import { expect, test } from '@playwright/test';
+
+import { seedBlankDocument } from '@documenso/prisma/seed/documents';
+import { seedUser } from '@documenso/prisma/seed/users';
+
+import { apiSignin } from '../fixtures/authentication';
+
+test('[DOCUMENT_FLOW]: Simple duplicate recipients test', async ({ page }) => {
+  const { user, team } = await seedUser();
+  const document = await seedBlankDocument(user, team.id);
+
+  await apiSignin({
+    page,
+    email: user.email,
+    redirectPath: `/t/${team.url}/documents/${document.id}/edit`,
+  });
+
+  // Step 1: Settings - Continue with defaults
+  await page.getByRole('button', { name: 'Continue' }).click();
+  await expect(page.getByRole('heading', { name: 'Add Signers' })).toBeVisible();
+
+  // Step 2: Add duplicate recipients
+  await page.getByPlaceholder('Email').fill('duplicate@example.com');
+  await page.getByPlaceholder('Name').fill('Duplicate 1');
+
+  await page.getByRole('button', { name: 'Add Signer' }).click();
+  await page.getByLabel('Email').nth(1).fill('duplicate@example.com');
+  await page.getByLabel('Name').nth(1).fill('Duplicate 2');
+
+  // Continue to fields
+  await page.getByRole('button', { name: 'Continue' }).click();
+  await expect(page.getByRole('heading', { name: 'Add Fields' })).toBeVisible();
+
+  // Step 3: Add fields
+  await page.getByRole('button', { name: 'Signature' }).click();
+  await page.locator('canvas').click({ position: { x: 100, y: 100 } });
+
+  await page.getByRole('combobox').first().click();
+
+  // Switch to second duplicate and add field
+  await page.getByText('Duplicate 2 (duplicate@example.com)').first().click();
+  await page.getByRole('button', { name: 'Signature' }).click();
+  await page.locator('canvas').click({ position: { x: 200, y: 100 } });
+
+  // Continue to send
+  await page.getByRole('button', { name: 'Continue' }).click();
+  await expect(page.getByRole('heading', { name: 'Distribute Document' })).toBeVisible();
+
+  // Send document
+  await page.waitForTimeout(2500);
+  await page.getByRole('button', { name: 'Send' }).click();
+
+  await page.waitForURL(new RegExp(`/t/${team.url}/documents/\\d+`));
+
+  await expect(page.getByRole('link', { name: document.title })).toBeVisible();
+});

packages/app-tests/e2e/document-flow/duplicate-recipients.spec.ts

@@ -0,0 +1,355 @@
+import { type Page, expect, test } from '@playwright/test';
+import type { Document, Team } from '@prisma/client';
+
+import { PDF_VIEWER_PAGE_SELECTOR } from '@documenso/lib/constants/pdf-viewer';
+import { prisma } from '@documenso/prisma';
+import { seedBlankDocument } from '@documenso/prisma/seed/documents';
+import { seedUser } from '@documenso/prisma/seed/users';
+
+import { apiSignin } from '../fixtures/authentication';
+import { signSignaturePad } from '../fixtures/signature';
+
+/**
+ * Test helper to complete the document creation flow with duplicate recipients
+ */
+const completeDocumentFlowWithDuplicateRecipients = async (options: {
+  page: Page;
+  team: Team;
+  document: Document;
+}) => {
+  const { page, team, document } = options;
+
+  // Step 1: Settings - Continue with defaults
+  await page.getByRole('button', { name: 'Continue' }).click();
+  await expect(page.getByRole('heading', { name: 'Add Signers' })).toBeVisible();
+
+  // Step 2: Add duplicate recipients
+  await page.getByPlaceholder('Email').fill('duplicate@example.com');
+  await page.getByPlaceholder('Name').fill('Duplicate Recipient 1');
+
+  // Add second signer with same email
+  await page.getByRole('button', { name: 'Add Signer' }).click();
+  await page.getByLabel('Email').nth(1).fill('duplicate@example.com');
+  await page.getByLabel('Name').nth(1).fill('Duplicate Recipient 2');
+
+  // Add third signer with different email for comparison
+  await page.getByRole('button', { name: 'Add Signer' }).click();
+  await page.getByLabel('Email').nth(2).fill('unique@example.com');
+  await page.getByLabel('Name').nth(2).fill('Unique Recipient');
+
+  // Continue to fields
+  await page.getByRole('button', { name: 'Continue' }).click();
+  await expect(page.getByRole('heading', { name: 'Add Fields' })).toBeVisible();
+
+  // Step 3: Add fields for each recipient
+  // Add signature field for first duplicate recipient
+  await page.getByRole('button', { name: 'Signature' }).click();
+  await page.locator('canvas').click({ position: { x: 100, y: 100 } });
+
+  await page.getByText('Duplicate Recipient 1 (duplicate@example.com)').click();
+
+  // Switch to second duplicate recipient and add their field
+  await page.getByText('Duplicate Recipient 2 (duplicate@example.com)').click();
+  await page.getByRole('button', { name: 'Signature' }).click();
+  await page.locator('canvas').click({ position: { x: 200, y: 100 } });
+
+  await page.getByText('Duplicate Recipient 2 (duplicate@example.com)').click();
+
+  // Switch to unique recipient and add their field
+  await page.getByText('Unique Recipient (unique@example.com)').click();
+  await page.getByRole('button', { name: 'Signature' }).click();
+  await page.locator('canvas').click({ position: { x: 300, y: 100 } });
+
+  // Continue to subject
+  await page.getByRole('button', { name: 'Continue' }).click();
+  await expect(page.getByRole('heading', { name: 'Distribute Document' })).toBeVisible();
+
+  // Step 4: Complete with subject and send
+  await page.waitForTimeout(2500);
+  await page.getByRole('button', { name: 'Send' }).click();
+
+  // Wait for send confirmation
+  await page.waitForURL(new RegExp(`/t/${team.url}/documents/\\d+`));
+
+  await expect(page.getByRole('link', { name: document.title })).toBeVisible();
+};
+
+test.describe('[DOCUMENT_FLOW]: Duplicate Recipients', () => {
+  test('should allow creating document with duplicate recipient emails', async ({ page }) => {
+    const { user, team } = await seedUser();
+
+    const document = await seedBlankDocument(user, team.id);
+
+    await apiSignin({
+      page,
+      email: user.email,
+      redirectPath: `/t/${team.url}/documents/${document.id}/edit`,
+    });
+
+    // Complete the flow
+    await completeDocumentFlowWithDuplicateRecipients({
+      page,
+      team,
+      document,
+    });
+
+    // Verify document was created successfully
+    await expect(page).toHaveURL(new RegExp(`/t/${team.url}/documents`));
+  });
+
+  test('should allow adding duplicate recipient after saving document initially', async ({
+    page,
+  }) => {
+    const { user, team } = await seedUser();
+    const document = await seedBlankDocument(user, team.id);
+
+    await apiSignin({
+      page,
+      email: user.email,
+      redirectPath: `/t/${team.url}/documents/${document.id}/edit`,
+    });
+
+    // Step 1: Settings - Continue with defaults
+    await page.getByRole('button', { name: 'Continue' }).click();
+    await expect(page.getByRole('heading', { name: 'Add Signers' })).toBeVisible();
+
+    // Step 2: Add initial recipient
+    await page.getByPlaceholder('Email').fill('test@example.com');
+    await page.getByPlaceholder('Name').fill('Test Recipient');
+
+    // Continue to fields and add a field
+    await page.getByRole('button', { name: 'Continue' }).click();
+    await expect(page.getByRole('heading', { name: 'Add Fields' })).toBeVisible();
+
+    await page.getByRole('button', { name: 'Signature' }).click();
+    await page.locator('canvas').click({ position: { x: 100, y: 100 } });
+
+    // Save the document by going to subject
+    await page.getByRole('button', { name: 'Continue' }).click();
+    await expect(page.getByRole('heading', { name: 'Distribute Document' })).toBeVisible();
+
+    // Navigate back to signers to add duplicate
+    await page.getByRole('button', { name: 'Go Back' }).click();
+    await page.getByRole('button', { name: 'Go Back' }).click();
+    await expect(page.getByRole('heading', { name: 'Add Signers' })).toBeVisible();
+
+    // Add duplicate recipient
+    await page.getByRole('button', { name: 'Add Signer' }).click();
+    await page.getByLabel('Email').nth(1).fill('test@example.com');
+    await page.getByLabel('Name').nth(1).fill('Test Recipient Duplicate');
+
+    // Continue and add field for duplicate
+    await page.getByRole('button', { name: 'Continue' }).click();
+    await expect(page.getByRole('heading', { name: 'Add Fields' })).toBeVisible();
+
+    await page.waitForTimeout(1000);
+
+    // Switch to duplicate recipient and add field
+    await page.getByRole('combobox').first().click();
+    await page.getByText('Test Recipient Duplicate (test@example.com)').first().click();
+
+    await page.getByRole('button', { name: 'Signature' }).click();
+    await page.locator('canvas').click({ position: { x: 200, y: 100 } });
+
+    // Complete the flow
+    await page.getByRole('button', { name: 'Continue' }).click();
+    await expect(page.getByRole('heading', { name: 'Distribute Document' })).toBeVisible();
+    await page.waitForTimeout(2500);
+    await page.getByRole('button', { name: 'Send' }).click();
+
+    await page.waitForURL(new RegExp(`/t/${team.url}/documents/\\d+`));
+
+    await expect(page.getByRole('link', { name: document.title })).toBeVisible();
+  });
+
+  test('should isolate fields per recipient token even with duplicate emails', async ({
+    page,
+    context,
+  }) => {
+    const { user, team } = await seedUser();
+
+    const document = await seedBlankDocument(user, team.id);
+
+    await apiSignin({
+      page,
+      email: user.email,
+      redirectPath: `/t/${team.url}/documents/${document.id}/edit`,
+    });
+
+    // Complete the document flow
+    await completeDocumentFlowWithDuplicateRecipients({
+      page,
+      team,
+      document,
+    });
+
+    // Navigate to documents list and get the document
+    await expect(page).toHaveURL(new RegExp(`/t/${team.url}/documents`));
+
+    const recipients = await prisma.recipient.findMany({
+      where: {
+        documentId: document.id,
+      },
+    });
+
+    expect(recipients).toHaveLength(3);
+
+    const tokens = recipients.map((r) => r.token);
+
+    expect(new Set(tokens).size).toBe(3); // All tokens should be unique
+
+    // Test each signing experience in separate browser contexts
+    for (const recipient of recipients) {
+      // Navigate to signing URL
+      await page.goto(`/sign/${recipient.token}`, {
+        waitUntil: 'networkidle',
+      });
+
+      await page.waitForSelector(PDF_VIEWER_PAGE_SELECTOR);
+
+      // Verify only one signature field is visible for this recipient
+      expect(
+        await page.locator(`[data-field-type="SIGNATURE"]:not([data-readonly="true"])`).all(),
+      ).toHaveLength(1);
+
+      // Verify recipient name is correct
+      await expect(page.getByLabel('Full Name')).toHaveValue(recipient.name);
+
+      // Sign the document
+      await signSignaturePad(page);
+
+      await page
+        .locator('[data-field-type="SIGNATURE"]:not([data-readonly="true"])')
+        .first()
+        .click();
+
+      await page.getByRole('button', { name: 'Complete' }).click();
+      await page.getByRole('button', { name: 'Sign' }).click();
+
+      // Verify completion
+      await page.waitForURL(`/sign/${recipient?.token}/complete`);
+      await expect(page.getByText('Document Signed')).toBeVisible();
+    }
+  });
+
+  test('should handle duplicate recipient workflow with different field types', async ({
+    page,
+  }) => {
+    const { user, team } = await seedUser();
+    const document = await seedBlankDocument(user, team.id);
+
+    await apiSignin({
+      page,
+      email: user.email,
+      redirectPath: `/t/${team.url}/documents/${document.id}/edit`,
+    });
+
+    // Step 1: Settings
+    await page.getByRole('button', { name: 'Continue' }).click();
+
+    // Step 2: Add duplicate recipients with different roles
+    await page.getByPlaceholder('Email').fill('signer@example.com');
+    await page.getByPlaceholder('Name').fill('Signer Role');
+
+    await page.getByRole('button', { name: 'Add Signer' }).click();
+    await page.getByLabel('Email').nth(1).fill('signer@example.com');
+    await page.getByLabel('Name').nth(1).fill('Approver Role');
+
+    // Change second recipient role if role selector is available
+    const roleDropdown = page.getByLabel('Role').nth(1);
+
+    if (await roleDropdown.isVisible()) {
+      await roleDropdown.click();
+      await page.getByText('Approver').click();
+    }
+
+    // Step 3: Add different field types for each duplicate
+    await page.getByRole('button', { name: 'Continue' }).click();
+
+    // Add signature for first recipient
+    await page.getByRole('button', { name: 'Signature' }).click();
+    await page.locator('canvas').click({ position: { x: 100, y: 100 } });
+
+    // Add name field for second recipient
+    await page.getByRole('combobox').first().click();
+
+    await page.getByText('Approver Role (signer@example.com)').first().click();
+    await page.getByRole('button', { name: 'Name' }).click();
+    await page.locator('canvas').click({ position: { x: 200, y: 100 } });
+
+    // Add date field for second recipient
+    await page.getByRole('button', { name: 'Date' }).click();
+    await page.locator('canvas').click({ position: { x: 200, y: 150 } });
+
+    // Complete the document
+    await page.getByRole('button', { name: 'Continue' }).click();
+
+    await page.getByRole('button', { name: 'Send' }).click();
+
+    await page.waitForURL(new RegExp(`/t/${team.url}/documents/\\d+`));
+
+    await expect(page.getByRole('link', { name: document.title })).toBeVisible();
+  });
+
+  test('should preserve field assignments when editing document with duplicates', async ({
+    page,
+  }) => {
+    const { user, team } = await seedUser();
+    const document = await seedBlankDocument(user, team.id);
+
+    await apiSignin({
+      page,
+      email: user.email,
+      redirectPath: `/t/${team.url}/documents/${document.id}/edit`,
+    });
+
+    // Create document with duplicates and fields
+    await completeDocumentFlowWithDuplicateRecipients({
+      page,
+      team,
+      document,
+    });
+
+    // Navigate back to edit the document
+    await page.goto(`/t/${team.url}/documents/${document.id}/edit`);
+
+    // Go to fields step
+    await page.getByRole('button', { name: 'Continue' }).click(); // Settings
+    await page.getByRole('button', { name: 'Continue' }).click(); // Signers
+
+    // Verify fields are assigned to correct recipients
+    await expect(page.getByRole('heading', { name: 'Add Fields' })).toBeVisible();
+
+    // Click on first duplicate recipient
+    await page.getByText('Duplicate Recipient 1 (duplicate@example.com)').click();
+
+    // Verify their field is visible and can be selected
+    const firstRecipientFields = await page
+      .locator(`[data-field-type="SIGNATURE"]:not(:disabled)`)
+      .all();
+    expect(firstRecipientFields.length).toBeGreaterThan(0);
+
+    // Switch to second duplicate recipient
+    await page.getByText('Duplicate Recipient 2 (duplicate@example.com)').click();
+
+    // Verify they have their own field
+    const secondRecipientFields = await page
+      .locator(`[data-field-type="SIGNATURE"]:not(:disabled)`)
+      .all();
+    expect(secondRecipientFields.length).toBeGreaterThan(0);
+
+    // Add another field to the second duplicate
+    await page.getByRole('button', { name: 'Name' }).click();
+    await page.locator('canvas').click({ position: { x: 250, y: 150 } });
+
+    // Save changes
+    await page.getByRole('button', { name: 'Continue' }).click();
+    await expect(page.getByRole('heading', { name: 'Distribute Document' })).toBeVisible();
+    await page.waitForTimeout(2500);
+    await page.getByRole('button', { name: 'Send' }).click();
+
+    await page.waitForURL(new RegExp(`/t/${team.url}/documents/\\d+`));
+
+    await expect(page.getByRole('link', { name: document.title })).toBeVisible();
+  });
+});

packages/app-tests/e2e/document-flow/stepper-component.spec.ts

@@ -573,6 +573,7 @@ test('[DOCUMENT_FLOW]: should be able to create and sign a document with 3 recip
         y: 100 * i,
       },
     });
+
     await page.getByText(`User ${i} (user${i}@example.com)`).click();
   }
 

packages/app-tests/e2e/folders/team-account-folders.spec.ts

@@ -277,13 +277,13 @@ test('[TEAMS]: document folder and its contents can be deleted', async ({ page }
 
   await page.goto(`/t/${team.url}/documents`);
 
-  await expect(page.locator('div').filter({ hasText: folder.name })).not.toBeVisible();
+  await expect(page.locator(`[data-folder-id="${folder.id}"]`)).not.toBeVisible();
   await expect(page.getByText(proposal.title)).not.toBeVisible();
 
   await page.goto(`/t/${team.url}/documents/f/${folder.id}`);
 
   await expect(page.getByText(report.title)).not.toBeVisible();
-  await expect(page.locator('div').filter({ hasText: reportsFolder.name })).not.toBeVisible();
+  await expect(page.locator(`[data-folder-id="${reportsFolder.id}"]`)).not.toBeVisible();
 });
 
 test('[TEAMS]: create folder button is visible on templates page', async ({ page }) => {
@@ -318,9 +318,7 @@ test('[TEAMS]: can create a template folder', async ({ page }) => {
   await expect(page.getByText('Team template folder')).toBeVisible();
 
   await page.goto(`/t/${team.url}/templates`);
-  await expect(
-    page.locator('div').filter({ hasText: 'Team template folder' }).nth(3),
-  ).toBeVisible();
+  await expect(page.locator(`[data-folder-name="Team template folder"]`)).toBeVisible();
 });
 
 test('[TEAMS]: can create a template subfolder inside a template folder', async ({ page }) => {
@@ -374,11 +372,8 @@ test('[TEAMS]: can create a template inside a template folder', async ({ page })
 
   await page.getByRole('button', { name: 'New Template' }).click();
 
-  await page
-    .locator('div')
-    .filter({ hasText: /^Upload Template DocumentDrag & drop your PDF here\.$/ })
-    .nth(2)
-    .click();
+  await page.getByText('Upload Template Document').click();
+
   await page.locator('input[type="file"]').nth(0).waitFor({ state: 'attached' });
 
   await page
@@ -537,7 +532,7 @@ test('[TEAMS]: template folder can be moved to another template folder', async (
   await expect(page.getByText('Team Contract Templates')).toBeVisible();
 });
 
-test('[TEAMS]: template folder and its contents can be deleted', async ({ page }) => {
+test('[TEAMS]: template folder can be deleted', async ({ page }) => {
   const { team, teamOwner } = await seedTeamDocuments();
 
   const folder = await seedBlankFolder(teamOwner, team.id, {
@@ -585,13 +580,16 @@ test('[TEAMS]: template folder and its contents can be deleted', async ({ page }
 
   await page.goto(`/t/${team.url}/templates`);
 
-  await expect(page.locator('div').filter({ hasText: folder.name })).not.toBeVisible();
-  await expect(page.getByText(template.title)).not.toBeVisible();
+  await page.waitForTimeout(1000);
+
+  // !: This is no longer the case, when deleting a folder its contents will be moved to the root folder.
+  // await expect(page.locator(`[data-folder-id="${folder.id}"]`)).not.toBeVisible();
+  // await expect(page.getByText(template.title)).not.toBeVisible();
 
   await page.goto(`/t/${team.url}/templates/f/${folder.id}`);
 
   await expect(page.getByText(reportTemplate.title)).not.toBeVisible();
-  await expect(page.locator('div').filter({ hasText: subfolder.name })).not.toBeVisible();
+  await expect(page.locator(`[data-folder-id="${subfolder.id}"]`)).not.toBeVisible();
 });
 
 test('[TEAMS]: can navigate between template folders', async ({ page }) => {
@@ -843,10 +841,15 @@ test('[TEAMS]: documents inherit folder visibility', async ({ page }) => {
 
   await page.getByText('Admin Only Folder').click();
 
-  const fileInput = page.locator('input[type="file"]').nth(1);
-  await fileInput.waitFor({ state: 'attached' });
+  await page.waitForURL(new RegExp(`/t/${team.url}/documents/f/.+`));
 
-  await fileInput.setInputFiles(
+  // Upload document.
+  const [fileChooser] = await Promise.all([
+    page.waitForEvent('filechooser'),
+    page.getByRole('button', { name: 'Upload Document' }).click(),
+  ]);
+
+  await fileChooser.setFiles(
     path.join(__dirname, '../../../assets/documenso-supporter-pledge.pdf'),
   );
 

packages/app-tests/e2e/organisations/organisation-team-preferences.spec.ts

@@ -30,8 +30,8 @@ test('[ORGANISATIONS]: manage document preferences', async ({ page }) => {
   await page.getByRole('option', { name: 'Australia/Perth' }).click();
 
   // Set default date
-  await page.getByRole('combobox').filter({ hasText: 'yyyy-MM-dd hh:mm a' }).click();
-  await page.getByRole('option', { name: 'DD/MM/YYYY' }).click();
+  await page.getByRole('combobox').filter({ hasText: 'yyyy-MM-dd hh:mm AM/PM' }).click();
+  await page.getByRole('option', { name: 'DD/MM/YYYY', exact: true }).click();
 
   await page.getByTestId('signature-types-trigger').click();
   await page.getByRole('option', { name: 'Draw' }).click();
@@ -51,7 +51,7 @@ test('[ORGANISATIONS]: manage document preferences', async ({ page }) => {
   expect(teamSettings.documentVisibility).toEqual(DocumentVisibility.MANAGER_AND_ABOVE);
   expect(teamSettings.documentLanguage).toEqual('de');
   expect(teamSettings.documentTimezone).toEqual('Australia/Perth');
-  expect(teamSettings.documentDateFormat).toEqual('dd/MM/yyyy hh:mm a');
+  expect(teamSettings.documentDateFormat).toEqual('dd/MM/yyyy');
   expect(teamSettings.includeSenderDetails).toEqual(false);
   expect(teamSettings.includeSigningCertificate).toEqual(false);
   expect(teamSettings.typedSignatureEnabled).toEqual(true);
@@ -72,7 +72,7 @@ test('[ORGANISATIONS]: manage document preferences', async ({ page }) => {
 
   // Override team date format settings
   await page.getByTestId('document-date-format-trigger').click();
-  await page.getByRole('option', { name: 'MM/DD/YYYY' }).click();
+  await page.getByRole('option', { name: 'MM/DD/YYYY', exact: true }).click();
 
   await page.getByRole('button', { name: 'Update' }).first().click();
   await expect(page.getByText('Your document preferences have been updated').first()).toBeVisible();
@@ -85,7 +85,7 @@ test('[ORGANISATIONS]: manage document preferences', async ({ page }) => {
   expect(updatedTeamSettings.documentVisibility).toEqual(DocumentVisibility.EVERYONE);
   expect(updatedTeamSettings.documentLanguage).toEqual('pl');
   expect(updatedTeamSettings.documentTimezone).toEqual('Europe/London');
-  expect(updatedTeamSettings.documentDateFormat).toEqual('MM/dd/yyyy hh:mm a');
+  expect(updatedTeamSettings.documentDateFormat).toEqual('MM/dd/yyyy');
   expect(updatedTeamSettings.includeSenderDetails).toEqual(false);
   expect(updatedTeamSettings.includeSigningCertificate).toEqual(false);
   expect(updatedTeamSettings.typedSignatureEnabled).toEqual(true);
@@ -108,7 +108,7 @@ test('[ORGANISATIONS]: manage document preferences', async ({ page }) => {
   expect(documentMeta.drawSignatureEnabled).toEqual(false);
   expect(documentMeta.language).toEqual('pl');
   expect(documentMeta.timezone).toEqual('Europe/London');
-  expect(documentMeta.dateFormat).toEqual('MM/dd/yyyy hh:mm a');
+  expect(documentMeta.dateFormat).toEqual('MM/dd/yyyy');
 });
 
 test('[ORGANISATIONS]: manage branding preferences', async ({ page }) => {

packages/app-tests/e2e/templates-flow/duplicate-recipients.spec.ts

@@ -0,0 +1,283 @@
+import { type Page, expect, test } from '@playwright/test';
+import type { Team, Template } from '@prisma/client';
+
+import { PDF_VIEWER_PAGE_SELECTOR } from '@documenso/lib/constants/pdf-viewer';
+import { prisma } from '@documenso/prisma';
+import { seedBlankTemplate } from '@documenso/prisma/seed/templates';
+import { seedUser } from '@documenso/prisma/seed/users';
+
+import { apiSignin } from '../fixtures/authentication';
+
+/**
+ * Test helper to complete template creation with duplicate recipients
+ */
+const completeTemplateFlowWithDuplicateRecipients = async (options: {
+  page: Page;
+  team: Team;
+  template: Template;
+}) => {
+  const { page, team, template } = options;
+  // Step 1: Settings - Continue with defaults
+  await page.getByRole('button', { name: 'Continue' }).click();
+  await expect(page.getByRole('heading', { name: 'Add Placeholders' })).toBeVisible();
+
+  // Step 2: Add duplicate recipients with real emails for testing
+  await page.getByPlaceholder('Email').fill('duplicate@example.com');
+  await page.getByPlaceholder('Name').fill('First Instance');
+
+  // Add second signer with same email
+  await page.getByRole('button', { name: 'Add Placeholder Recipient' }).click();
+  await page.getByPlaceholder('Email').nth(1).fill('duplicate@example.com');
+  await page.getByPlaceholder('Name').nth(1).fill('Second Instance');
+
+  // Add third signer with different email
+  await page.getByRole('button', { name: 'Add Placeholder Recipient' }).click();
+  await page.getByPlaceholder('Email').nth(2).fill('unique@example.com');
+  await page.getByPlaceholder('Name').nth(2).fill('Different Recipient');
+
+  // Continue to fields
+  await page.getByRole('button', { name: 'Continue' }).click();
+  await expect(page.getByRole('heading', { name: 'Add Fields' })).toBeVisible();
+
+  // Step 3: Add fields for each recipient instance
+  // Add signature field for first instance
+  await page.getByRole('button', { name: 'Signature' }).click();
+  await page.locator('canvas').click({ position: { x: 100, y: 100 } });
+
+  // Switch to second instance and add their field
+  await page.getByRole('combobox').first().click();
+  await page.getByText('Second Instance').first().click();
+  await page.getByRole('button', { name: 'Signature' }).click();
+  await page.locator('canvas').click({ position: { x: 200, y: 100 } });
+
+  // Switch to different recipient and add their field
+  await page.getByRole('combobox').first().click();
+  await page.getByText('Different Recipient').first().click();
+  await page.getByRole('button', { name: 'Name' }).click();
+  await page.locator('canvas').click({ position: { x: 300, y: 100 } });
+
+  // Save template
+  await page.getByRole('button', { name: 'Save Template' }).click();
+
+  // Wait for creation confirmation
+  await page.waitForURL(`/t/${team.url}/templates`);
+  await expect(page.getByRole('link', { name: template.title })).toBeVisible();
+};
+
+test.describe('[TEMPLATE_FLOW]: Duplicate Recipients', () => {
+  test('should allow creating template with duplicate recipient emails', async ({ page }) => {
+    const { user, team } = await seedUser();
+
+    const template = await seedBlankTemplate(user, team.id);
+
+    await apiSignin({
+      page,
+      email: user.email,
+      redirectPath: `/t/${team.url}/templates/${template.id}/edit`,
+    });
+
+    // Complete the template flow
+    await completeTemplateFlowWithDuplicateRecipients({ page, team, template });
+
+    // Verify template was created successfully
+    await expect(page).toHaveURL(`/t/${team.url}/templates`);
+  });
+
+  test('should create document from template with duplicate recipients using same email', async ({
+    page,
+    context,
+  }) => {
+    const { user, team } = await seedUser();
+
+    const template = await seedBlankTemplate(user, team.id);
+
+    await apiSignin({
+      page,
+      email: user.email,
+      redirectPath: `/t/${team.url}/templates/${template.id}/edit`,
+    });
+
+    // Complete template creation
+    await completeTemplateFlowWithDuplicateRecipients({ page, team, template });
+
+    // Navigate to template and create document
+    await page.goto(`/t/${team.url}/templates`);
+
+    await page
+      .getByRole('row', { name: template.title })
+      .getByRole('button', { name: 'Use Template' })
+      .click();
+
+    // Fill recipient information with same email for both instances
+    await expect(page.getByRole('heading', { name: 'Create document' })).toBeVisible();
+
+    // Set same email for both recipient instances
+    const emailInputs = await page.locator('[aria-label="Email"]').all();
+    const nameInputs = await page.locator('[aria-label="Name"]').all();
+
+    // First instance
+    await emailInputs[0].fill('same@example.com');
+    await nameInputs[0].fill('John Doe - Role 1');
+
+    // Second instance (same email)
+    await emailInputs[1].fill('same@example.com');
+    await nameInputs[1].fill('John Doe - Role 2');
+
+    // Different recipient
+    await emailInputs[2].fill('different@example.com');
+    await nameInputs[2].fill('Jane Smith');
+
+    await page.getByLabel('Send document').click();
+
+    // Create document
+    await page.getByRole('button', { name: 'Create and send' }).click();
+    await page.waitForURL(new RegExp(`/t/${team.url}/documents/\\d+`));
+
+    // Get the document ID from URL for database queries
+    const url = page.url();
+    const documentIdMatch = url.match(/\/documents\/(\d+)/);
+
+    const documentId = documentIdMatch ? parseInt(documentIdMatch[1]) : null;
+
+    expect(documentId).not.toBeNull();
+
+    // Get recipients directly from database
+    const recipients = await prisma.recipient.findMany({
+      where: {
+        documentId: documentId!,
+      },
+    });
+
+    expect(recipients).toHaveLength(3);
+
+    // Verify all tokens are unique
+    const tokens = recipients.map((r) => r.token);
+    expect(new Set(tokens).size).toBe(3);
+
+    // Test signing experience for duplicate email recipients
+    const duplicateRecipients = recipients.filter((r) => r.email === 'same@example.com');
+    expect(duplicateRecipients).toHaveLength(2);
+
+    for (const recipient of duplicateRecipients) {
+      // Navigate to signing URL
+      await page.goto(`/sign/${recipient.token}`, {
+        waitUntil: 'networkidle',
+      });
+
+      await page.waitForSelector(PDF_VIEWER_PAGE_SELECTOR);
+
+      // Verify correct recipient name is shown
+      await expect(page.getByLabel('Full Name')).toHaveValue(recipient.name);
+
+      // Verify only one signature field is visible for this recipient
+      expect(
+        await page.locator(`[data-field-type="SIGNATURE"]:not([data-readonly="true"])`).all(),
+      ).toHaveLength(1);
+    }
+  });
+
+  test('should handle template with different types of duplicate emails', async ({ page }) => {
+    const { user, team } = await seedUser();
+
+    const template = await seedBlankTemplate(user, team.id);
+
+    await apiSignin({
+      page,
+      email: user.email,
+      redirectPath: `/t/${team.url}/templates/${template.id}/edit`,
+    });
+
+    // Step 1: Settings
+    await page.getByRole('button', { name: 'Continue' }).click();
+
+    // Step 2: Add multiple recipients with duplicate emails
+    await page.getByPlaceholder('Email').fill('duplicate@example.com');
+    await page.getByPlaceholder('Name').fill('Duplicate Recipient 1');
+
+    await page.getByRole('button', { name: 'Add Placeholder Recipient' }).click();
+    await page.getByPlaceholder('Email').nth(1).fill('duplicate@example.com');
+    await page.getByPlaceholder('Name').nth(1).fill('Duplicate Recipient 2');
+
+    await page.getByRole('button', { name: 'Add Placeholder Recipient' }).click();
+    await page.getByPlaceholder('Email').nth(2).fill('different@example.com');
+    await page.getByPlaceholder('Name').nth(2).fill('Different Recipient');
+
+    // Continue and add fields
+    await page.getByRole('button', { name: 'Continue' }).click();
+
+    // Add fields for each recipient
+    await page.getByRole('button', { name: 'Signature' }).click();
+    await page.locator('canvas').click({ position: { x: 100, y: 100 } });
+
+    await page.getByRole('combobox').first().click();
+    await page.getByText('Duplicate Recipient 2').first().click();
+    await page.getByRole('button', { name: 'Date' }).click();
+    await page.locator('canvas').click({ position: { x: 200, y: 100 } });
+
+    await page.getByRole('combobox').first().click();
+    await page.getByText('Different Recipient').first().click();
+    await page.getByRole('button', { name: 'Name' }).click();
+    await page.locator('canvas').click({ position: { x: 100, y: 200 } });
+
+    // Save template
+    await page.getByRole('button', { name: 'Save Template' }).click();
+
+    await page.waitForURL(`/t/${team.url}/templates`);
+
+    await expect(page.getByRole('link', { name: template.title })).toBeVisible();
+  });
+
+  test('should validate field assignments per recipient in template editing', async ({ page }) => {
+    const { user, team } = await seedUser();
+
+    const template = await seedBlankTemplate(user, team.id);
+
+    await apiSignin({
+      page,
+      email: user.email,
+      redirectPath: `/t/${team.url}/templates/${template.id}/edit`,
+    });
+
+    // Create template with duplicates
+    await completeTemplateFlowWithDuplicateRecipients({ page, team, template });
+
+    // Navigate back to edit the template
+    await page.goto(`/t/${team.url}/templates/${template.id}/edit`);
+
+    // Go to fields step
+    await page.getByRole('button', { name: 'Continue' }).click(); // Settings
+    await page.getByRole('button', { name: 'Continue' }).click(); // Signers
+
+    await expect(page.getByRole('heading', { name: 'Add Fields' })).toBeVisible();
+
+    // Verify fields are correctly assigned to each recipient instance
+    await page.getByRole('combobox').first().click();
+    await page.getByRole('option', { name: 'First Instance' }).first().click();
+    let visibleFields = await page.locator(`[data-field-type="SIGNATURE"]:not(:disabled)`).all();
+    expect(visibleFields.length).toBeGreaterThan(0);
+
+    await page.getByRole('combobox').first().click();
+    await page.getByRole('option', { name: 'Second Instance' }).first().click();
+    visibleFields = await page.locator(`[data-field-type="SIGNATURE"]:not(:disabled)`).all();
+    expect(visibleFields.length).toBeGreaterThan(0);
+
+    await page.getByRole('combobox').first().click();
+    await page.getByRole('option', { name: 'Different Recipient' }).first().click();
+    const nameFields = await page.locator(`[data-field-type="NAME"]:not(:disabled)`).all();
+    expect(nameFields.length).toBeGreaterThan(0);
+
+    // Add additional field to verify proper assignment
+    await page.getByRole('combobox').first().click();
+    await page.getByRole('option', { name: 'First Instance' }).first().click();
+    await page.getByRole('button', { name: 'Name' }).click();
+    await page.locator('canvas').click({ position: { x: 100, y: 300 } });
+
+    await page.waitForTimeout(2500);
+
+    // Save changes
+    await page.getByRole('button', { name: 'Save Template' }).click();
+
+    await page.waitForURL(`/t/${team.url}/templates`);
+    await expect(page.getByRole('link', { name: template.title })).toBeVisible();
+  });
+});

packages/app-tests/e2e/templates-flow/template-autosave-fields-step.spec.ts

@@ -33,7 +33,7 @@ const setupTemplateAndNavigateToFieldsStep = async (page: Page) => {
 };
 
 const triggerAutosave = async (page: Page) => {
-  await page.locator('#document-flow-form-container').click();
+  await page.locator('body').click({ position: { x: 0, y: 0 } });
   await page.locator('#document-flow-form-container').blur();
 
   await page.waitForTimeout(5000);
@@ -70,7 +70,7 @@ test.describe('AutoSave Fields Step', () => {
 
     await triggerAutosave(page);
 
-    await page.getByRole('combobox').click();
+    await page.getByRole('combobox').first().click();
     await page.getByRole('option', { name: 'Recipient 2 (recipient2@documenso.com)' }).click();
 
     await page.getByRole('button', { name: 'Signature' }).click();
@@ -129,7 +129,7 @@ test.describe('AutoSave Fields Step', () => {
 
     await triggerAutosave(page);
 
-    await page.getByRole('combobox').click();
+    await page.getByRole('combobox').first().click();
     await page.getByRole('option', { name: 'Recipient 2 (recipient2@documenso.com)' }).click();
 
     await page.getByRole('button', { name: 'Signature' }).click();
@@ -142,7 +142,7 @@ test.describe('AutoSave Fields Step', () => {
 
     await triggerAutosave(page);
 
-    await page.getByRole('combobox').click();
+    await page.getByRole('combobox').first().click();
     await page.getByRole('option', { name: 'Recipient 1 (recipient1@documenso.com)' }).click();
 
     await page.getByText('Text').nth(1).click();
@@ -195,7 +195,7 @@ test.describe('AutoSave Fields Step', () => {
 
     await triggerAutosave(page);
 
-    await page.getByRole('combobox').click();
+    await page.getByRole('combobox').first().click();
     await page.getByRole('option', { name: 'Recipient 2 (recipient2@documenso.com)' }).click();
 
     await page.getByRole('button', { name: 'Signature' }).click();
@@ -208,7 +208,7 @@ test.describe('AutoSave Fields Step', () => {
 
     await triggerAutosave(page);
 
-    await page.getByRole('combobox').click();
+    await page.getByRole('combobox').first().click();
     await page.getByRole('option', { name: 'Recipient 1 (recipient1@documenso.com)' }).click();
 
     await page.getByText('Signature').nth(1).click();

packages/app-tests/e2e/templates-flow/template-autosave-settings-step.spec.ts

@@ -23,7 +23,7 @@ const setupTemplate = async (page: Page) => {
 };
 
 const triggerAutosave = async (page: Page) => {
-  await page.locator('#document-flow-form-container').click();
+  await page.locator('body').click({ position: { x: 0, y: 0 } });
   await page.locator('#document-flow-form-container').blur();
 
   await page.waitForTimeout(5000);

packages/app-tests/e2e/templates-flow/template-autosave-signers-step.spec.ts

@@ -26,7 +26,7 @@ const setupTemplateAndNavigateToSignersStep = async (page: Page) => {
 };
 
 const triggerAutosave = async (page: Page) => {
-  await page.locator('#document-flow-form-container').click();
+  await page.locator('body').click({ position: { x: 0, y: 0 } });
   await page.locator('#document-flow-form-container').blur();
 
   await page.waitForTimeout(5000);

packages/app-tests/e2e/templates/create-document-from-template.spec.ts

@@ -47,8 +47,8 @@ test('[TEMPLATE]: should create a document from a template', async ({ page }) =>
 
   // Set advanced options.
   await page.getByRole('button', { name: 'Advanced Options' }).click();
-  await page.locator('button').filter({ hasText: 'YYYY-MM-DD HH:mm a' }).click();
-  await page.getByLabel('DD/MM/YYYY').click();
+  await page.locator('button').filter({ hasText: 'YYYY-MM-DD hh:mm AM/PM' }).click();
+  await page.getByLabel('DD/MM/YYYY HH:mm', { exact: true }).click();
 
   await page.locator('.time-zone-field').click();
   await page.getByRole('option', { name: 'Etc/UTC' }).click();
@@ -96,7 +96,7 @@ test('[TEMPLATE]: should create a document from a template', async ({ page }) =>
   expect(document.title).toEqual('TEMPLATE_TITLE');
   expect(documentAuth.documentAuthOption.globalAccessAuth).toContain('ACCOUNT');
 
-  expect(document.documentMeta?.dateFormat).toEqual('dd/MM/yyyy hh:mm a');
+  expect(document.documentMeta?.dateFormat).toEqual('dd/MM/yyyy HH:mm');
   expect(document.documentMeta?.message).toEqual('MESSAGE');
   expect(document.documentMeta?.redirectUrl).toEqual('https://documenso.com');
   expect(document.documentMeta?.subject).toEqual('SUBJECT');
@@ -150,8 +150,8 @@ test('[TEMPLATE]: should create a team document from a team template', async ({
 
   // Set advanced options.
   await page.getByRole('button', { name: 'Advanced Options' }).click();
-  await page.locator('button').filter({ hasText: 'YYYY-MM-DD HH:mm a' }).click();
-  await page.getByLabel('DD/MM/YYYY').click();
+  await page.locator('button').filter({ hasText: 'YYYY-MM-DD hh:mm AM/PM' }).click();
+  await page.getByLabel('DD/MM/YYYY HH:mm', { exact: true }).click();
 
   await page.locator('.time-zone-field').click();
   await page.getByRole('option', { name: 'Etc/UTC' }).click();
@@ -200,7 +200,7 @@ test('[TEMPLATE]: should create a team document from a team template', async ({
 
   expect(document.title).toEqual('TEMPLATE_TITLE');
   expect(documentAuth.documentAuthOption.globalAccessAuth).toContain('ACCOUNT');
-  expect(document.documentMeta?.dateFormat).toEqual('dd/MM/yyyy hh:mm a');
+  expect(document.documentMeta?.dateFormat).toEqual('dd/MM/yyyy HH:mm');
   expect(document.documentMeta?.message).toEqual('MESSAGE');
   expect(document.documentMeta?.redirectUrl).toEqual('https://documenso.com');
   expect(document.documentMeta?.subject).toEqual('SUBJECT');

packages/app-tests/playwright.config.ts

@@ -17,7 +17,7 @@ export default defineConfig({
   testDir: './e2e',
   /* Run tests in files in parallel */
   fullyParallel: false,
-  workers: 4,
+  workers: 2,
   maxFailures: process.env.CI ? 1 : undefined,
   /* Fail the build on CI if you accidentally left test.only in the source code. */
   forbidOnly: !!process.env.CI,
@@ -33,7 +33,7 @@ export default defineConfig({
     /* Collect trace when retrying the failed test. See https://playwright.dev/docs/trace-viewer */
     trace: 'on',
 
-    video: 'retain-on-failure',
+    video: 'on-first-retry',
 
     /* Add explicit timeouts for actions */
     actionTimeout: 15_000,
@@ -48,7 +48,7 @@ export default defineConfig({
       name: 'chromium',
       use: {
         ...devices['Desktop Chrome'],
-        viewport: { width: 1920, height: 1080 },
+        viewport: { width: 1920, height: 1200 },
       },
     },
 

packages/auth/server/lib/utils/handle-oauth-authorize-url.ts

@@ -23,12 +23,17 @@ type HandleOAuthAuthorizeUrlOptions = {
    * Optional redirect path to redirect the user somewhere on the app after authorization.
    */
   redirectPath?: string;
+
+  /**
+   * Optional prompt to pass to the authorization endpoint.
+   */
+  prompt?: 'login' | 'consent' | 'select_account';
 };
 
 const oauthCookieMaxAge = 60 * 10; // 10 minutes.
 
 export const handleOAuthAuthorizeUrl = async (options: HandleOAuthAuthorizeUrlOptions) => {
-  const { c, clientOptions, redirectPath } = options;
+  const { c, clientOptions, redirectPath, prompt = 'login' } = options;
 
   if (!clientOptions.clientId || !clientOptions.clientSecret) {
     throw new AppError(AppErrorCode.NOT_SETUP);
@@ -57,8 +62,8 @@ export const handleOAuthAuthorizeUrl = async (options: HandleOAuthAuthorizeUrlOp
     scopes,
   );
 
-  // Allow user to select account during login.
-  url.searchParams.append('prompt', 'login');
+  // Pass the prompt to the authorization endpoint.
+  url.searchParams.append('prompt', prompt);
 
   setCookie(c, `${clientOptions.id}_oauth_state`, state, {
     ...sessionCookieOptions,

packages/auth/server/routes/oauth.ts

@@ -50,5 +50,6 @@ export const oauthRoute = new Hono<HonoAuthContext>()
     return await handleOAuthAuthorizeUrl({
       c,
       clientOptions,
+      prompt: 'select_account',
     });
   });

packages/email/template-components/template-access-auth-2fa.tsx

@@ -0,0 +1,60 @@
+import { Trans } from '@lingui/react/macro';
+
+import { Heading, Img, Section, Text } from '../components';
+
+export type TemplateAccessAuth2FAProps = {
+  documentTitle: string;
+  code: string;
+  userEmail: string;
+  userName: string;
+  expiresInMinutes: number;
+  assetBaseUrl?: string;
+};
+
+export const TemplateAccessAuth2FA = ({
+  documentTitle,
+  code,
+  userName,
+  expiresInMinutes,
+  assetBaseUrl = 'http://localhost:3002',
+}: TemplateAccessAuth2FAProps) => {
+  const getAssetUrl = (path: string) => {
+    return new URL(path, assetBaseUrl).toString();
+  };
+
+  return (
+    <div>
+      <Img src={getAssetUrl('/static/document.png')} alt="Document" className="mx-auto h-12 w-12" />
+
+      <Section className="mt-8">
+        <Heading className="text-center text-lg font-semibold text-slate-900">
+          <Trans>Verification Code Required</Trans>
+        </Heading>
+
+        <Text className="mt-2 text-center text-slate-700">
+          <Trans>
+            Hi {userName}, you need to enter a verification code to complete the document "
+            {documentTitle}".
+          </Trans>
+        </Text>
+
+        <Section className="mt-6 rounded-lg bg-slate-50 p-6 text-center">
+          <Text className="mb-2 text-sm font-medium text-slate-600">
+            <Trans>Your verification code:</Trans>
+          </Text>
+          <Text className="text-2xl font-bold tracking-wider text-slate-900">{code}</Text>
+        </Section>
+
+        <Text className="mt-4 text-center text-sm text-slate-600">
+          <Trans>This code will expire in {expiresInMinutes} minutes.</Trans>
+        </Text>
+
+        <Text className="mt-4 text-center text-sm text-slate-500">
+          <Trans>
+            If you didn't request this verification code, you can safely ignore this email.
+          </Trans>
+        </Text>
+      </Section>
+    </div>
+  );
+};

packages/email/template-components/template-document-invite.tsx

@@ -1,5 +1,3 @@
-import { useMemo } from 'react';
-
 import { useLingui } from '@lingui/react';
 import { Trans } from '@lingui/react/macro';
 import { OrganisationType, RecipientRole } from '@prisma/client';
@@ -38,12 +36,6 @@ export const TemplateDocumentInvite = ({
 
   const { actionVerb } = RECIPIENT_ROLES_DESCRIPTION[role];
 
-  const rejectDocumentLink = useMemo(() => {
-    const url = new URL(signDocumentLink);
-    url.searchParams.set('reject', 'true');
-    return url.toString();
-  }, [signDocumentLink]);
-
   return (
     <>
       <TemplateDocumentImage className="mt-6" assetBaseUrl={assetBaseUrl} />
@@ -99,22 +91,15 @@ export const TemplateDocumentInvite = ({
 
         <Section className="mb-6 mt-8 text-center">
           <Button
-            className="mr-4 inline-flex items-center justify-center rounded-lg bg-red-500 px-6 py-3 text-center text-sm font-medium text-black no-underline"
-            href={rejectDocumentLink}
-          >
-            <Trans>Reject Document</Trans>
-          </Button>
-
-          <Button
-            className="bg-documenso-500 inline-flex items-center justify-center rounded-lg px-6 py-3 text-center text-sm font-medium text-black no-underline"
+            className="bg-documenso-500 text-sbase inline-flex items-center justify-center rounded-lg px-6 py-3 text-center font-medium text-black no-underline"
             href={signDocumentLink}
           >
             {match(role)
-              .with(RecipientRole.SIGNER, () => <Trans>Sign Document</Trans>)
+              .with(RecipientRole.SIGNER, () => <Trans>View Document to sign</Trans>)
               .with(RecipientRole.VIEWER, () => <Trans>View Document</Trans>)
-              .with(RecipientRole.APPROVER, () => <Trans>Approve Document</Trans>)
+              .with(RecipientRole.APPROVER, () => <Trans>View Document to approve</Trans>)
               .with(RecipientRole.CC, () => '')
-              .with(RecipientRole.ASSISTANT, () => <Trans>Assist Document</Trans>)
+              .with(RecipientRole.ASSISTANT, () => <Trans>View Document to assist</Trans>)
               .exhaustive()}
           </Button>
         </Section>

packages/email/templates/access-auth-2fa.tsx

@@ -0,0 +1,77 @@
+import { msg } from '@lingui/core/macro';
+import { useLingui } from '@lingui/react';
+
+import { Body, Container, Head, Html, Img, Preview, Section } from '../components';
+import { useBranding } from '../providers/branding';
+import { TemplateAccessAuth2FA } from '../template-components/template-access-auth-2fa';
+import { TemplateFooter } from '../template-components/template-footer';
+
+export type AccessAuth2FAEmailTemplateProps = {
+  documentTitle: string;
+  code: string;
+  userEmail: string;
+  userName: string;
+  expiresInMinutes: number;
+  assetBaseUrl?: string;
+};
+
+export const AccessAuth2FAEmailTemplate = ({
+  documentTitle,
+  code,
+  userEmail,
+  userName,
+  expiresInMinutes,
+  assetBaseUrl = 'http://localhost:3002',
+}: AccessAuth2FAEmailTemplateProps) => {
+  const { _ } = useLingui();
+
+  const branding = useBranding();
+
+  const previewText = msg`Your verification code is ${code}`;
+
+  const getAssetUrl = (path: string) => {
+    return new URL(path, assetBaseUrl).toString();
+  };
+
+  return (
+    <Html>
+      <Head />
+      <Preview>{_(previewText)}</Preview>
+
+      <Body className="mx-auto my-auto bg-white font-sans">
+        <Section>
+          <Container className="mx-auto mb-2 mt-8 max-w-xl rounded-lg border border-solid border-slate-200 p-4 backdrop-blur-sm">
+            <Section>
+              {branding.brandingEnabled && branding.brandingLogo ? (
+                <Img src={branding.brandingLogo} alt="Branding Logo" className="mb-4 h-6" />
+              ) : (
+                <Img
+                  src={getAssetUrl('/static/logo.png')}
+                  alt="Documenso Logo"
+                  className="mb-4 h-6"
+                />
+              )}
+
+              <TemplateAccessAuth2FA
+                documentTitle={documentTitle}
+                code={code}
+                userEmail={userEmail}
+                userName={userName}
+                expiresInMinutes={expiresInMinutes}
+                assetBaseUrl={assetBaseUrl}
+              />
+            </Section>
+          </Container>
+
+          <div className="mx-auto mt-12 max-w-xl" />
+
+          <Container className="mx-auto max-w-xl">
+            <TemplateFooter isDocument={false} />
+          </Container>
+        </Section>
+      </Body>
+    </Html>
+  );
+};
+
+export default AccessAuth2FAEmailTemplate;

packages/lib/client-only/hooks/use-autosave.ts

@@ -1,23 +1,56 @@
 import { useCallback, useEffect, useRef } from 'react';
 
-export const useAutoSave = <T>(onSave: (data: T) => Promise<void>) => {
-  const saveTimeoutRef = useRef<NodeJS.Timeout>();
+type SaveRequest<T, R> = {
+  data: T;
+  onResponse?: (response: R) => void;
+};
 
-  const saveFormData = async (data: T) => {
-    try {
-      await onSave(data);
-    } catch (error) {
-      console.error('Auto-save failed:', error);
+export const useAutoSave = <T, R = void>(
+  onSave: (data: T) => Promise<R>,
+  options: { delay?: number } = {},
+) => {
+  const { delay = 2000 } = options;
+
+  const saveTimeoutRef = useRef<NodeJS.Timeout>();
+  const saveQueueRef = useRef<SaveRequest<T, R>[]>([]);
+  const isProcessingRef = useRef(false);
+
+  const processQueue = async () => {
+    if (isProcessingRef.current || saveQueueRef.current.length === 0) {
+      return;
     }
+
+    isProcessingRef.current = true;
+
+    while (saveQueueRef.current.length > 0) {
+      const request = saveQueueRef.current.shift()!;
+
+      try {
+        const response = await onSave(request.data);
+        request.onResponse?.(response);
+      } catch (error) {
+        console.error('Auto-save failed:', error);
+      }
+    }
+
+    isProcessingRef.current = false;
   };
 
-  const scheduleSave = useCallback((data: T) => {
-    if (saveTimeoutRef.current) {
-      clearTimeout(saveTimeoutRef.current);
-    }
+  const saveFormData = async (data: T, onResponse?: (response: R) => void) => {
+    saveQueueRef.current.push({ data, onResponse });
+    await processQueue();
+  };
 
-    saveTimeoutRef.current = setTimeout(() => void saveFormData(data), 2000);
-  }, []);
+  const scheduleSave = useCallback(
+    (data: T, onResponse?: (response: R) => void) => {
+      if (saveTimeoutRef.current) {
+        clearTimeout(saveTimeoutRef.current);
+      }
+
+      saveTimeoutRef.current = setTimeout(() => void saveFormData(data, onResponse), delay);
+    },
+    [delay],
+  );
 
   useEffect(() => {
     return () => {

packages/lib/constants/date-formats.ts

@@ -7,14 +7,25 @@ export const DEFAULT_DOCUMENT_DATE_FORMAT = 'yyyy-MM-dd hh:mm a';
 export const VALID_DATE_FORMAT_VALUES = [
   DEFAULT_DOCUMENT_DATE_FORMAT,
   'yyyy-MM-dd',
+  'dd/MM/yyyy',
+  'MM/dd/yyyy',
+  'yy-MM-dd',
+  'MMMM dd, yyyy',
+  'EEEE, MMMM dd, yyyy',
   'dd/MM/yyyy hh:mm a',
+  'dd/MM/yyyy HH:mm',
   'MM/dd/yyyy hh:mm a',
+  'MM/dd/yyyy HH:mm',
+  'dd.MM.yyyy',
   'dd.MM.yyyy HH:mm',
   'yyyy-MM-dd HH:mm',
   'yy-MM-dd hh:mm a',
+  'yy-MM-dd HH:mm',
   'yyyy-MM-dd HH:mm:ss',
   'MMMM dd, yyyy hh:mm a',
+  'MMMM dd, yyyy HH:mm',
   'EEEE, MMMM dd, yyyy hh:mm a',
+  'EEEE, MMMM dd, yyyy HH:mm',
   "yyyy-MM-dd'T'HH:mm:ss.SSSXXX",
 ] as const;
 
@@ -22,10 +33,80 @@ export type ValidDateFormat = (typeof VALID_DATE_FORMAT_VALUES)[number];
 
 export const DATE_FORMATS = [
   {
-    key: 'yyyy-MM-dd_hh:mm_a',
-    label: 'YYYY-MM-DD HH:mm a',
+    key: 'yyyy-MM-dd_HH:mm_12H',
+    label: 'YYYY-MM-DD hh:mm AM/PM',
     value: DEFAULT_DOCUMENT_DATE_FORMAT,
   },
+  {
+    key: 'yyyy-MM-dd_HH:mm',
+    label: 'YYYY-MM-DD HH:mm',
+    value: 'yyyy-MM-dd HH:mm',
+  },
+  {
+    key: 'DDMMYYYY_TIME',
+    label: 'DD/MM/YYYY HH:mm',
+    value: 'dd/MM/yyyy HH:mm',
+  },
+  {
+    key: 'DDMMYYYY_TIME_12H',
+    label: 'DD/MM/YYYY HH:mm AM/PM',
+    value: 'dd/MM/yyyy hh:mm a',
+  },
+  {
+    key: 'MMDDYYYY_TIME',
+    label: 'MM/DD/YYYY HH:mm',
+    value: 'MM/dd/yyyy HH:mm',
+  },
+  {
+    key: 'MMDDYYYY_TIME_12H',
+    label: 'MM/DD/YYYY HH:mm AM/PM',
+    value: 'MM/dd/yyyy hh:mm a',
+  },
+  {
+    key: 'DDMMYYYYHHMM',
+    label: 'DD.MM.YYYY HH:mm',
+    value: 'dd.MM.yyyy HH:mm',
+  },
+  {
+    key: 'YYMMDD_TIME',
+    label: 'YY-MM-DD HH:mm',
+    value: 'yy-MM-dd HH:mm',
+  },
+  {
+    key: 'YYMMDD_TIME_12H',
+    label: 'YY-MM-DD HH:mm AM/PM',
+    value: 'yy-MM-dd hh:mm a',
+  },
+  {
+    key: 'YYYY_MM_DD_HH_MM_SS',
+    label: 'YYYY-MM-DD HH:mm:ss',
+    value: 'yyyy-MM-dd HH:mm:ss',
+  },
+  {
+    key: 'MonthDateYear_TIME',
+    label: 'Month Date, Year HH:mm',
+    value: 'MMMM dd, yyyy HH:mm',
+  },
+  {
+    key: 'MonthDateYear_TIME_12H',
+    label: 'Month Date, Year HH:mm AM/PM',
+    value: 'MMMM dd, yyyy hh:mm a',
+  },
+  {
+    key: 'DayMonthYear_TIME',
+    label: 'Day, Month Year HH:mm',
+    value: 'EEEE, MMMM dd, yyyy HH:mm',
+  },
+  {
+    key: 'DayMonthYear_TIME_12H',
+    label: 'Day, Month Year HH:mm AM/PM',
+    value: 'EEEE, MMMM dd, yyyy hh:mm a',
+  },
+  {
+    key: 'ISO8601',
+    label: 'ISO 8601',
+    value: "yyyy-MM-dd'T'HH:mm:ss.SSSXXX",
+  },
   {
     key: 'YYYYMMDD',
     label: 'YYYY-MM-DD',
@@ -34,47 +115,32 @@ export const DATE_FORMATS = [
   {
     key: 'DDMMYYYY',
     label: 'DD/MM/YYYY',
-    value: 'dd/MM/yyyy hh:mm a',
+    value: 'dd/MM/yyyy',
   },
   {
     key: 'MMDDYYYY',
     label: 'MM/DD/YYYY',
-    value: 'MM/dd/yyyy hh:mm a',
+    value: 'MM/dd/yyyy',
   },
   {
-    key: 'DDMMYYYYHHMM',
-    label: 'DD.MM.YYYY HH:mm',
-    value: 'dd.MM.yyyy HH:mm',
-  },
-  {
-    key: 'YYYYMMDDHHmm',
-    label: 'YYYY-MM-DD HH:mm',
-    value: 'yyyy-MM-dd HH:mm',
+    key: 'DDMMYYYY_DOT',
+    label: 'DD.MM.YYYY',
+    value: 'dd.MM.yyyy',
   },
   {
     key: 'YYMMDD',
     label: 'YY-MM-DD',
-    value: 'yy-MM-dd hh:mm a',
-  },
-  {
-    key: 'YYYYMMDDhhmmss',
-    label: 'YYYY-MM-DD HH:mm:ss',
-    value: 'yyyy-MM-dd HH:mm:ss',
+    value: 'yy-MM-dd',
   },
   {
     key: 'MonthDateYear',
     label: 'Month Date, Year',
-    value: 'MMMM dd, yyyy hh:mm a',
+    value: 'MMMM dd, yyyy',
   },
   {
     key: 'DayMonthYear',
     label: 'Day, Month Year',
-    value: 'EEEE, MMMM dd, yyyy hh:mm a',
-  },
-  {
-    key: 'ISO8601',
-    label: 'ISO 8601',
-    value: "yyyy-MM-dd'T'HH:mm:ss.SSSXXX",
+    value: 'EEEE, MMMM dd, yyyy',
   },
 ] satisfies {
   key: string;

packages/lib/errors/app-error.ts

@@ -17,6 +17,7 @@ export enum AppErrorCode {
   'RETRY_EXCEPTION' = 'RETRY_EXCEPTION',
   'SCHEMA_FAILED' = 'SCHEMA_FAILED',
   'TOO_MANY_REQUESTS' = 'TOO_MANY_REQUESTS',
+  'TWO_FACTOR_AUTH_FAILED' = 'TWO_FACTOR_AUTH_FAILED',
 }
 
 export const genericErrorCodeToTrpcErrorCodeMap: Record<string, { code: string; status: number }> =
@@ -32,6 +33,7 @@ export const genericErrorCodeToTrpcErrorCodeMap: Record<string, { code: string;
     [AppErrorCode.RETRY_EXCEPTION]: { code: 'INTERNAL_SERVER_ERROR', status: 500 },
     [AppErrorCode.SCHEMA_FAILED]: { code: 'INTERNAL_SERVER_ERROR', status: 500 },
     [AppErrorCode.TOO_MANY_REQUESTS]: { code: 'TOO_MANY_REQUESTS', status: 429 },
+    [AppErrorCode.TWO_FACTOR_AUTH_FAILED]: { code: 'UNAUTHORIZED', status: 401 },
   };
 
 export const ZAppErrorJsonSchema = z.object({

packages/lib/server-only/2fa/email/constants.ts

@@ -0,0 +1 @@
+export const TWO_FACTOR_EMAIL_EXPIRATION_MINUTES = 5;

packages/lib/server-only/2fa/email/generate-2fa-credentials-from-email.ts

@@ -0,0 +1,38 @@
+import { hmac } from '@noble/hashes/hmac';
+import { sha256 } from '@noble/hashes/sha256';
+import { createTOTPKeyURI } from 'oslo/otp';
+
+import { DOCUMENSO_ENCRYPTION_KEY } from '../../../constants/crypto';
+
+const ISSUER = 'Documenso Email 2FA';
+
+export type GenerateTwoFactorCredentialsFromEmailOptions = {
+  documentId: number;
+  email: string;
+};
+
+/**
+ * Generate an encrypted token containing a 6-digit 2FA code for email verification.
+ *
+ * @param options - The options for generating the token
+ * @returns Object containing the token and the 6-digit code
+ */
+export const generateTwoFactorCredentialsFromEmail = ({
+  documentId,
+  email,
+}: GenerateTwoFactorCredentialsFromEmailOptions) => {
+  if (!DOCUMENSO_ENCRYPTION_KEY) {
+    throw new Error('Missing DOCUMENSO_ENCRYPTION_KEY');
+  }
+
+  const identity = `email-2fa|v1|email:${email}|id:${documentId}`;
+
+  const secret = hmac(sha256, DOCUMENSO_ENCRYPTION_KEY, identity);
+
+  const uri = createTOTPKeyURI(ISSUER, email, secret);
+
+  return {
+    uri,
+    secret,
+  };
+};

packages/lib/server-only/2fa/email/generate-2fa-token-from-email.ts

@@ -0,0 +1,23 @@
+import { generateHOTP } from 'oslo/otp';
+
+import { generateTwoFactorCredentialsFromEmail } from './generate-2fa-credentials-from-email';
+
+export type GenerateTwoFactorTokenFromEmailOptions = {
+  documentId: number;
+  email: string;
+  period?: number;
+};
+
+export const generateTwoFactorTokenFromEmail = async ({
+  email,
+  documentId,
+  period = 30_000,
+}: GenerateTwoFactorTokenFromEmailOptions) => {
+  const { secret } = generateTwoFactorCredentialsFromEmail({ email, documentId });
+
+  const counter = Math.floor(Date.now() / period);
+
+  const token = await generateHOTP(secret, counter);
+
+  return token;
+};

packages/lib/server-only/2fa/email/send-2fa-token-email.ts

@@ -0,0 +1,124 @@
+import { createElement } from 'react';
+
+import { msg } from '@lingui/core/macro';
+
+import { mailer } from '@documenso/email/mailer';
+import { AccessAuth2FAEmailTemplate } from '@documenso/email/templates/access-auth-2fa';
+import { prisma } from '@documenso/prisma';
+
+import { getI18nInstance } from '../../../client-only/providers/i18n-server';
+import { NEXT_PUBLIC_WEBAPP_URL } from '../../../constants/app';
+import { AppError, AppErrorCode } from '../../../errors/app-error';
+import { DOCUMENT_AUDIT_LOG_TYPE } from '../../../types/document-audit-logs';
+import { createDocumentAuditLogData } from '../../../utils/document-audit-logs';
+import { renderEmailWithI18N } from '../../../utils/render-email-with-i18n';
+import { getEmailContext } from '../../email/get-email-context';
+import { TWO_FACTOR_EMAIL_EXPIRATION_MINUTES } from './constants';
+import { generateTwoFactorTokenFromEmail } from './generate-2fa-token-from-email';
+
+export type Send2FATokenEmailOptions = {
+  token: string;
+  documentId: number;
+};
+
+export const send2FATokenEmail = async ({ token, documentId }: Send2FATokenEmailOptions) => {
+  const document = await prisma.document.findFirst({
+    where: {
+      id: documentId,
+      recipients: {
+        some: {
+          token,
+        },
+      },
+    },
+    include: {
+      recipients: {
+        where: {
+          token,
+        },
+      },
+      documentMeta: true,
+      team: {
+        select: {
+          teamEmail: true,
+          name: true,
+        },
+      },
+    },
+  });
+
+  if (!document) {
+    throw new AppError(AppErrorCode.NOT_FOUND, {
+      message: 'Document not found',
+    });
+  }
+
+  const [recipient] = document.recipients;
+
+  if (!recipient) {
+    throw new AppError(AppErrorCode.NOT_FOUND, {
+      message: 'Recipient not found',
+    });
+  }
+
+  const twoFactorTokenToken = await generateTwoFactorTokenFromEmail({
+    documentId,
+    email: recipient.email,
+  });
+
+  const { branding, emailLanguage, senderEmail, replyToEmail } = await getEmailContext({
+    emailType: 'RECIPIENT',
+    source: {
+      type: 'team',
+      teamId: document.teamId,
+    },
+    meta: document.documentMeta,
+  });
+
+  const i18n = await getI18nInstance(emailLanguage);
+
+  const subject = i18n._(msg`Your two-factor authentication code`);
+
+  const template = createElement(AccessAuth2FAEmailTemplate, {
+    documentTitle: document.title,
+    userName: recipient.name,
+    userEmail: recipient.email,
+    code: twoFactorTokenToken,
+    expiresInMinutes: TWO_FACTOR_EMAIL_EXPIRATION_MINUTES,
+    assetBaseUrl: NEXT_PUBLIC_WEBAPP_URL(),
+  });
+
+  const [html, text] = await Promise.all([
+    renderEmailWithI18N(template, { lang: emailLanguage, branding }),
+    renderEmailWithI18N(template, { lang: emailLanguage, branding, plainText: true }),
+  ]);
+
+  await prisma.$transaction(
+    async (tx) => {
+      await mailer.sendMail({
+        to: {
+          address: recipient.email,
+          name: recipient.name,
+        },
+        from: senderEmail,
+        replyTo: replyToEmail,
+        subject,
+        html,
+        text,
+      });
+
+      await tx.documentAuditLog.create({
+        data: createDocumentAuditLogData({
+          type: DOCUMENT_AUDIT_LOG_TYPE.DOCUMENT_ACCESS_AUTH_2FA_REQUESTED,
+          documentId: document.id,
+          data: {
+            recipientEmail: recipient.email,
+            recipientName: recipient.name,
+            recipientId: recipient.id,
+          },
+        }),
+      });
+    },
+    { timeout: 30_000 },
+  );
+};

packages/lib/server-only/2fa/email/validate-2fa-token-from-email.ts

@@ -0,0 +1,37 @@
+import { generateHOTP } from 'oslo/otp';
+
+import { generateTwoFactorCredentialsFromEmail } from './generate-2fa-credentials-from-email';
+
+export type ValidateTwoFactorTokenFromEmailOptions = {
+  documentId: number;
+  email: string;
+  code: string;
+  period?: number;
+  window?: number;
+};
+
+export const validateTwoFactorTokenFromEmail = async ({
+  documentId,
+  email,
+  code,
+  period = 30_000,
+  window = 1,
+}: ValidateTwoFactorTokenFromEmailOptions) => {
+  const { secret } = generateTwoFactorCredentialsFromEmail({ email, documentId });
+
+  let now = Date.now();
+
+  for (let i = 0; i < window; i++) {
+    const counter = Math.floor(now / period);
+
+    const hotp = await generateHOTP(secret, counter);
+
+    if (code === hotp) {
+      return true;
+    }
+
+    now -= period;
+  }
+
+  return false;
+};

packages/lib/server-only/cert/cert-status.ts

@@ -2,18 +2,25 @@ import * as fs from 'node:fs';
 
 import { env } from '@documenso/lib/utils/env';
 
-export type CertificateStatus = {
-  isAvailable: boolean;
-};
+export const getCertificateStatus = () => {
+  if (env('NEXT_PRIVATE_SIGNING_TRANSPORT') !== 'local') {
+    return { isAvailable: true };
+  }
+
+  if (env('NEXT_PRIVATE_SIGNING_LOCAL_FILE_CONTENTS')) {
+    return { isAvailable: true };
+  }
 
-export const getCertificateStatus = (): CertificateStatus => {
   const defaultPath =
     env('NODE_ENV') === 'production' ? '/opt/documenso/cert.p12' : './example/cert.p12';
+
   const filePath = env('NEXT_PRIVATE_SIGNING_LOCAL_FILE_PATH') || defaultPath;
 
   try {
     fs.accessSync(filePath, fs.constants.F_OK | fs.constants.R_OK);
+
     const stats = fs.statSync(filePath);
+
     return { isAvailable: stats.size > 0 };
   } catch {
     return { isAvailable: false };

packages/lib/server-only/document/complete-document-with-token.ts

@@ -18,7 +18,8 @@ import { prisma } from '@documenso/prisma';
 
 import { AppError, AppErrorCode } from '../../errors/app-error';
 import { jobs } from '../../jobs/client';
-import type { TRecipientActionAuth } from '../../types/document-auth';
+import type { TRecipientAccessAuth, TRecipientActionAuth } from '../../types/document-auth';
+import { DocumentAuth } from '../../types/document-auth';
 import {
   ZWebhookDocumentSchema,
   mapDocumentToWebhookDocumentPayload,
@@ -26,6 +27,7 @@ import {
 import { extractDocumentAuthMethods } from '../../utils/document-auth';
 import { getIsRecipientsTurnToSign } from '../recipient/get-is-recipient-turn';
 import { triggerWebhook } from '../webhooks/trigger/trigger-webhook';
+import { isRecipientAuthorized } from './is-recipient-authorized';
 import { sendPendingEmail } from './send-pending-email';
 
 export type CompleteDocumentWithTokenOptions = {
@@ -33,6 +35,7 @@ export type CompleteDocumentWithTokenOptions = {
   documentId: number;
   userId?: number;
   authOptions?: TRecipientActionAuth;
+  accessAuthOptions?: TRecipientAccessAuth;
   requestMetadata?: RequestMetadata;
   nextSigner?: {
     email: string;
@@ -64,6 +67,8 @@ const getDocument = async ({ token, documentId }: CompleteDocumentWithTokenOptio
 export const completeDocumentWithToken = async ({
   token,
   documentId,
+  userId,
+  accessAuthOptions,
   requestMetadata,
   nextSigner,
 }: CompleteDocumentWithTokenOptions) => {
@@ -111,24 +116,57 @@ export const completeDocumentWithToken = async ({
     throw new Error(`Recipient ${recipient.id} has unsigned fields`);
   }
 
-  // Document reauth for completing documents is currently not required.
+  // Check ACCESS AUTH 2FA validation during document completion
+  const { derivedRecipientAccessAuth } = extractDocumentAuthMethods({
+    documentAuth: document.authOptions,
+    recipientAuth: recipient.authOptions,
+  });
 
-  // const { derivedRecipientActionAuth } = extractDocumentAuthMethods({
-  //   documentAuth: document.authOptions,
-  //   recipientAuth: recipient.authOptions,
-  // });
+  if (derivedRecipientAccessAuth.includes(DocumentAuth.TWO_FACTOR_AUTH)) {
+    if (!accessAuthOptions) {
+      throw new AppError(AppErrorCode.UNAUTHORIZED, {
+        message: 'Access authentication required',
+      });
+    }
 
-  // const isValid = await isRecipientAuthorized({
-  //   type: 'ACTION',
-  //   document: document,
-  //   recipient: recipient,
-  //   userId,
-  //   authOptions,
-  // });
+    const isValid = await isRecipientAuthorized({
+      type: 'ACCESS_2FA',
+      documentAuthOptions: document.authOptions,
+      recipient: recipient,
+      userId, // Can be undefined for non-account recipients
+      authOptions: accessAuthOptions,
+    });
 
-  // if (!isValid) {
-  //   throw new AppError(AppErrorCode.UNAUTHORIZED, 'Invalid authentication values');
-  // }
+    if (!isValid) {
+      await prisma.documentAuditLog.create({
+        data: createDocumentAuditLogData({
+          type: DOCUMENT_AUDIT_LOG_TYPE.DOCUMENT_ACCESS_AUTH_2FA_FAILED,
+          documentId: document.id,
+          data: {
+            recipientId: recipient.id,
+            recipientName: recipient.name,
+            recipientEmail: recipient.email,
+          },
+        }),
+      });
+
+      throw new AppError(AppErrorCode.TWO_FACTOR_AUTH_FAILED, {
+        message: 'Invalid 2FA authentication',
+      });
+    }
+
+    await prisma.documentAuditLog.create({
+      data: createDocumentAuditLogData({
+        type: DOCUMENT_AUDIT_LOG_TYPE.DOCUMENT_ACCESS_AUTH_2FA_VALIDATED,
+        documentId: document.id,
+        data: {
+          recipientId: recipient.id,
+          recipientName: recipient.name,
+          recipientEmail: recipient.email,
+        },
+      }),
+    });
+  }
 
   await prisma.$transaction(async (tx) => {
     await tx.recipient.update({

packages/lib/server-only/document/get-document-by-token.ts

@@ -92,6 +92,12 @@ export const getDocumentAndSenderByToken = async ({
         select: {
           name: true,
           teamEmail: true,
+          teamGlobalSettings: {
+            select: {
+              brandingEnabled: true,
+              brandingLogo: true,
+            },
+          },
         },
       },
     },

packages/lib/server-only/document/is-recipient-authorized.ts

@@ -4,6 +4,7 @@ import { match } from 'ts-pattern';
 
 import { prisma } from '@documenso/prisma';
 
+import { validateTwoFactorTokenFromEmail } from '../2fa/email/validate-2fa-token-from-email';
 import { verifyTwoFactorAuthenticationToken } from '../2fa/verify-2fa-token';
 import { verifyPassword } from '../2fa/verify-password';
 import { AppError, AppErrorCode } from '../../errors/app-error';
@@ -14,9 +15,10 @@ import { getAuthenticatorOptions } from '../../utils/authenticator';
 import { extractDocumentAuthMethods } from '../../utils/document-auth';
 
 type IsRecipientAuthorizedOptions = {
-  type: 'ACCESS' | 'ACTION';
+  // !: Probably find a better name than 'ACCESS_2FA' if requirements change.
+  type: 'ACCESS' | 'ACCESS_2FA' | 'ACTION';
   documentAuthOptions: Document['authOptions'];
-  recipient: Pick<Recipient, 'authOptions' | 'email'>;
+  recipient: Pick<Recipient, 'authOptions' | 'email' | 'documentId'>;
 
   /**
    * The ID of the user who initiated the request.
@@ -61,8 +63,11 @@ export const isRecipientAuthorized = async ({
     recipientAuth: recipient.authOptions,
   });
 
-  const authMethods: TDocumentAuth[] =
-    type === 'ACCESS' ? derivedRecipientAccessAuth : derivedRecipientActionAuth;
+  const authMethods: TDocumentAuth[] = match(type)
+    .with('ACCESS', () => derivedRecipientAccessAuth)
+    .with('ACCESS_2FA', () => derivedRecipientAccessAuth)
+    .with('ACTION', () => derivedRecipientActionAuth)
+    .exhaustive();
 
   // Early true return when auth is not required.
   if (
@@ -72,6 +77,11 @@ export const isRecipientAuthorized = async ({
     return true;
   }
 
+  // Early true return for ACCESS auth if all methods are 2FA since validation happens in ACCESS_2FA.
+  if (type === 'ACCESS' && authMethods.every((method) => method === DocumentAuth.TWO_FACTOR_AUTH)) {
+    return true;
+  }
+
   // Create auth options when none are passed for account.
   if (!authOptions && authMethods.some((method) => method === DocumentAuth.ACCOUNT)) {
     authOptions = {
@@ -80,12 +90,16 @@ export const isRecipientAuthorized = async ({
   }
 
   // Authentication required does not match provided method.
-  if (!authOptions || !authMethods.includes(authOptions.type) || !userId) {
+  if (!authOptions || !authMethods.includes(authOptions.type)) {
     return false;
   }
 
   return await match(authOptions)
     .with({ type: DocumentAuth.ACCOUNT }, async () => {
+      if (!userId) {
+        return false;
+      }
+
       const recipientUser = await getUserByEmail(recipient.email);
 
       if (!recipientUser) {
@@ -95,13 +109,40 @@ export const isRecipientAuthorized = async ({
       return recipientUser.id === userId;
     })
     .with({ type: DocumentAuth.PASSKEY }, async ({ authenticationResponse, tokenReference }) => {
+      if (!userId) {
+        return false;
+      }
+
       return await isPasskeyAuthValid({
         userId,
         authenticationResponse,
         tokenReference,
       });
     })
-    .with({ type: DocumentAuth.TWO_FACTOR_AUTH }, async ({ token }) => {
+    .with({ type: DocumentAuth.TWO_FACTOR_AUTH }, async ({ token, method }) => {
+      if (type === 'ACCESS') {
+        return true;
+      }
+
+      if (type === 'ACCESS_2FA' && method === 'email') {
+        if (!recipient.documentId) {
+          throw new AppError(AppErrorCode.NOT_FOUND, {
+            message: 'Document ID is required for email 2FA verification',
+          });
+        }
+
+        return await validateTwoFactorTokenFromEmail({
+          documentId: recipient.documentId,
+          email: recipient.email,
+          code: token,
+          window: 10, // 5 minutes worth of tokens
+        });
+      }
+
+      if (!userId) {
+        return false;
+      }
+
       const user = await prisma.user.findFirst({
         where: {
           id: userId,
@@ -115,6 +156,7 @@ export const isRecipientAuthorized = async ({
         });
       }
 
+      // For ACTION auth or authenticator method, use TOTP
       return await verifyTwoFactorAuthenticationToken({
         user,
         totpCode: token,
@@ -122,6 +164,10 @@ export const isRecipientAuthorized = async ({
       });
     })
     .with({ type: DocumentAuth.PASSWORD }, async ({ password }) => {
+      if (!userId) {
+        return false;
+      }
+
       return await verifyPassword({
         userId,
         password,

packages/lib/server-only/document/search-documents-with-keyword.ts

@@ -1,6 +1,5 @@
-import { DocumentStatus } from '@prisma/client';
 import type { Document, Recipient, User } from '@prisma/client';
-import { DocumentVisibility, TeamMemberRole } from '@prisma/client';
+import { DocumentStatus, DocumentVisibility, TeamMemberRole } from '@prisma/client';
 import { match } from 'ts-pattern';
 
 import {
@@ -19,7 +18,7 @@ export type SearchDocumentsWithKeywordOptions = {
 export const searchDocumentsWithKeyword = async ({
   query,
   userId,
-  limit = 5,
+  limit = 20,
 }: SearchDocumentsWithKeywordOptions) => {
   const user = await prisma.user.findFirstOrThrow({
     where: {
@@ -122,6 +121,7 @@ export const searchDocumentsWithKeyword = async ({
         },
       },
     },
+    distinct: ['id'],
     orderBy: {
       createdAt: 'desc',
     },
@@ -129,6 +129,7 @@ export const searchDocumentsWithKeyword = async ({
   });
 
   const isOwner = (document: Document, user: User) => document.userId === user.id;
+
   const getSigningLink = (recipients: Recipient[], user: User) =>
     `/sign/${recipients.find((r) => r.email === user.email)?.token}`;
 
@@ -164,7 +165,7 @@ export const searchDocumentsWithKeyword = async ({
 
       if (isOwner(document, user)) {
         documentPath = `${formatDocumentsPath(document.team?.url)}/${document.id}`;
-      } else if (document.teamId && document.team) {
+      } else if (document.teamId && document.team.teamGroups.length > 0) {
         documentPath = `${formatDocumentsPath(document.team.url)}/${document.id}`;
       } else {
         documentPath = getSigningLink(recipients, user);

packages/lib/server-only/document/validate-field-auth.ts

@@ -7,7 +7,7 @@ import { isRecipientAuthorized } from './is-recipient-authorized';
 
 export type ValidateFieldAuthOptions = {
   documentAuthOptions: Document['authOptions'];
-  recipient: Pick<Recipient, 'authOptions' | 'email'>;
+  recipient: Pick<Recipient, 'authOptions' | 'email' | 'documentId'>;
   field: Field;
   userId?: number;
   authOptions?: TRecipientActionAuth;

packages/lib/server-only/field/set-fields-for-document.ts

@@ -84,9 +84,7 @@ export const setFieldsForDocument = async ({
   const linkedFields = fields.map((field) => {
     const existing = existingFields.find((existingField) => existingField.id === field.id);
 
-    const recipient = document.recipients.find(
-      (recipient) => recipient.email.toLowerCase() === field.signerEmail.toLowerCase(),
-    );
+    const recipient = document.recipients.find((recipient) => recipient.id === field.recipientId);
 
     // Each field MUST have a recipient associated with it.
     if (!recipient) {
@@ -226,10 +224,8 @@ export const setFieldsForDocument = async ({
             },
             recipient: {
               connect: {
-                documentId_email: {
-                  documentId,
-                  email: fieldSignerEmail,
-                },
+                id: field.recipientId,
+                documentId,
               },
             },
           },
@@ -330,6 +326,7 @@ type FieldData = {
   id?: number | null;
   type: FieldType;
   signerEmail: string;
+  recipientId: number;
   pageNumber: number;
   pageX: number;
   pageY: number;

packages/lib/server-only/field/set-fields-for-template.ts

@@ -26,6 +26,7 @@ export type SetFieldsForTemplateOptions = {
     id?: number | null;
     type: FieldType;
     signerEmail: string;
+    recipientId: number;
     pageNumber: number;
     pageX: number;
     pageY: number;
@@ -169,10 +170,8 @@ export const setFieldsForTemplate = async ({
           },
           recipient: {
             connect: {
-              templateId_email: {
-                templateId,
-                email: field.signerEmail.toLowerCase(),
-              },
+              id: field.recipientId,
+              templateId,
             },
           },
         },

packages/lib/server-only/recipient/create-document-recipients.ts

@@ -85,20 +85,6 @@ export const createDocumentRecipients = async ({
     email: recipient.email.toLowerCase(),
   }));
 
-  const duplicateRecipients = normalizedRecipients.filter((newRecipient) => {
-    const existingRecipient = document.recipients.find(
-      (existingRecipient) => existingRecipient.email === newRecipient.email,
-    );
-
-    return existingRecipient !== undefined;
-  });
-
-  if (duplicateRecipients.length > 0) {
-    throw new AppError(AppErrorCode.INVALID_REQUEST, {
-      message: `Duplicate recipient(s) found for ${duplicateRecipients.map((recipient) => recipient.email).join(', ')}`,
-    });
-  }
-
   const createdRecipients = await prisma.$transaction(async (tx) => {
     return await Promise.all(
       normalizedRecipients.map(async (recipient) => {

packages/lib/server-only/recipient/create-template-recipients.ts

@@ -71,20 +71,6 @@ export const createTemplateRecipients = async ({
     email: recipient.email.toLowerCase(),
   }));
 
-  const duplicateRecipients = normalizedRecipients.filter((newRecipient) => {
-    const existingRecipient = template.recipients.find(
-      (existingRecipient) => existingRecipient.email === newRecipient.email,
-    );
-
-    return existingRecipient !== undefined;
-  });
-
-  if (duplicateRecipients.length > 0) {
-    throw new AppError(AppErrorCode.INVALID_REQUEST, {
-      message: `Duplicate recipient(s) found for ${duplicateRecipients.map((recipient) => recipient.email).join(', ')}`,
-    });
-  }
-
   const createdRecipients = await prisma.$transaction(async (tx) => {
     return await Promise.all(
       normalizedRecipients.map(async (recipient) => {

packages/lib/server-only/recipient/set-document-recipients.ts

@@ -122,16 +122,12 @@ export const setDocumentRecipients = async ({
 
   const removedRecipients = existingRecipients.filter(
     (existingRecipient) =>
-      !normalizedRecipients.find(
-        (recipient) =>
-          recipient.id === existingRecipient.id || recipient.email === existingRecipient.email,
-      ),
+      !normalizedRecipients.find((recipient) => recipient.id === existingRecipient.id),
   );
 
   const linkedRecipients = normalizedRecipients.map((recipient) => {
     const existing = existingRecipients.find(
-      (existingRecipient) =>
-        existingRecipient.id === recipient.id || existingRecipient.email === recipient.email,
+      (existingRecipient) => existingRecipient.id === recipient.id,
     );
 
     const canPersistedRecipientBeModified =

packages/lib/server-only/recipient/set-template-recipients.ts

@@ -94,10 +94,7 @@ export const setTemplateRecipients = async ({
 
   const removedRecipients = existingRecipients.filter(
     (existingRecipient) =>
-      !normalizedRecipients.find(
-        (recipient) =>
-          recipient.id === existingRecipient.id || recipient.email === existingRecipient.email,
-      ),
+      !normalizedRecipients.find((recipient) => recipient.id === existingRecipient.id),
   );
 
   if (template.directLink !== null) {
@@ -124,8 +121,7 @@ export const setTemplateRecipients = async ({
 
   const linkedRecipients = normalizedRecipients.map((recipient) => {
     const existing = existingRecipients.find(
-      (existingRecipient) =>
-        existingRecipient.id === recipient.id || existingRecipient.email === recipient.email,
+      (existingRecipient) => existingRecipient.id === recipient.id,
     );
 
     return {

packages/lib/server-only/recipient/update-document-recipients.ts

@@ -91,17 +91,6 @@ export const updateDocumentRecipients = async ({
       });
     }
 
-    const duplicateRecipientWithSameEmail = document.recipients.find(
-      (existingRecipient) =>
-        existingRecipient.email === recipient.email && existingRecipient.id !== recipient.id,
-    );
-
-    if (duplicateRecipientWithSameEmail) {
-      throw new AppError(AppErrorCode.INVALID_REQUEST, {
-        message: `Duplicate recipient with the same email found: ${duplicateRecipientWithSameEmail.email}`,
-      });
-    }
-
     if (!canRecipientBeModified(originalRecipient, document.fields)) {
       throw new AppError(AppErrorCode.INVALID_REQUEST, {
         message: 'Cannot modify a recipient who has already interacted with the document',

packages/lib/server-only/recipient/update-template-recipients.ts

@@ -80,17 +80,6 @@ export const updateTemplateRecipients = async ({
       });
     }
 
-    const duplicateRecipientWithSameEmail = template.recipients.find(
-      (existingRecipient) =>
-        existingRecipient.email === recipient.email && existingRecipient.id !== recipient.id,
-    );
-
-    if (duplicateRecipientWithSameEmail) {
-      throw new AppError(AppErrorCode.INVALID_REQUEST, {
-        message: `Duplicate recipient with the same email found: ${duplicateRecipientWithSameEmail.email}`,
-      });
-    }
-
     return {
       originalRecipient,
       recipientUpdateData: recipient,

packages/lib/server-only/template/create-document-from-direct-template.ts

@@ -159,6 +159,7 @@ export const createDocumentFromDirectTemplate = async ({
   // Ensure typesafety when we add more options.
   const isAccessAuthValid = match(derivedRecipientAccessAuth.at(0))
     .with(DocumentAccessAuth.ACCOUNT, () => user && user?.email === directRecipientEmail)
+    .with(DocumentAccessAuth.TWO_FACTOR_AUTH, () => false) // Not supported for direct templates
     .with(undefined, () => true)
     .exhaustive();
 
@@ -205,6 +206,7 @@ export const createDocumentFromDirectTemplate = async ({
         recipient: {
           authOptions: directTemplateRecipient.authOptions,
           email: directRecipientEmail,
+          documentId: template.id,
         },
         field: templateField,
         userId: user?.id,

packages/lib/server-only/template/create-document-from-template-legacy.ts

@@ -19,6 +19,8 @@ export type CreateDocumentFromTemplateLegacyOptions = {
   }[];
 };
 
+// !TODO: Make this work
+
 /**
  * Legacy server function for /api/v1
  */
@@ -58,6 +60,15 @@ export const createDocumentFromTemplateLegacy = async ({
     },
   });
 
+  const recipientsToCreate = template.recipients.map((recipient) => ({
+    id: recipient.id,
+    email: recipient.email,
+    name: recipient.name,
+    role: recipient.role,
+    signingOrder: recipient.signingOrder,
+    token: nanoid(),
+  }));
+
   const document = await prisma.document.create({
     data: {
       qrToken: prefixedId('qr'),
@@ -70,12 +81,12 @@ export const createDocumentFromTemplateLegacy = async ({
       documentDataId: documentData.id,
       useLegacyFieldInsertion: template.useLegacyFieldInsertion ?? false,
       recipients: {
-        create: template.recipients.map((recipient) => ({
+        create: recipientsToCreate.map((recipient) => ({
           email: recipient.email,
           name: recipient.name,
           role: recipient.role,
           signingOrder: recipient.signingOrder,
-          token: nanoid(),
+          token: recipient.token,
         })),
       },
       documentMeta: {
@@ -95,9 +106,11 @@ export const createDocumentFromTemplateLegacy = async ({
 
   await prisma.field.createMany({
     data: template.fields.map((field) => {
-      const recipient = template.recipients.find((recipient) => recipient.id === field.recipientId);
+      const recipient = recipientsToCreate.find((recipient) => recipient.id === field.recipientId);
 
-      const documentRecipient = document.recipients.find((doc) => doc.email === recipient?.email);
+      const documentRecipient = document.recipients.find(
+        (documentRecipient) => documentRecipient.token === recipient?.token,
+      );
 
       if (!documentRecipient) {
         throw new Error('Recipient not found.');
@@ -118,28 +131,32 @@ export const createDocumentFromTemplateLegacy = async ({
     }),
   });
 
+  // Replicate the old logic, get by index and create if we exceed the number of existing recipients.
   if (recipients && recipients.length > 0) {
-    document.recipients = await Promise.all(
+    await Promise.all(
       recipients.map(async (recipient, index) => {
         const existingRecipient = document.recipients.at(index);
 
-        return await prisma.recipient.upsert({
-          where: {
-            documentId_email: {
+        if (existingRecipient) {
+          return await prisma.recipient.update({
+            where: {
+              id: existingRecipient.id,
               documentId: document.id,
-              email: existingRecipient?.email ?? recipient.email,
             },
-          },
-          update: {
-            name: recipient.name,
-            email: recipient.email,
-            role: recipient.role,
-            signingOrder: recipient.signingOrder,
-          },
-          create: {
+            data: {
+              name: recipient.name,
+              email: recipient.email,
+              role: recipient.role,
+              signingOrder: recipient.signingOrder,
+            },
+          });
+        }
+
+        return await prisma.recipient.create({
+          data: {
             documentId: document.id,
-            email: recipient.email,
             name: recipient.name,
+            email: recipient.email,
             role: recipient.role,
             signingOrder: recipient.signingOrder,
             token: nanoid(),
@@ -149,5 +166,18 @@ export const createDocumentFromTemplateLegacy = async ({
     );
   }
 
-  return document;
+  // Gross but we need to do the additional fetch since we mutate above.
+  const updatedRecipients = await prisma.recipient.findMany({
+    where: {
+      documentId: document.id,
+    },
+    orderBy: {
+      id: 'asc',
+    },
+  });
+
+  return {
+    ...document,
+    recipients: updatedRecipients,
+  };
 };

packages/lib/server-only/template/create-document-from-template.ts

@@ -53,7 +53,7 @@ import { triggerWebhook } from '../webhooks/trigger/trigger-webhook';
 
 type FinalRecipient = Pick<
   Recipient,
-  'name' | 'email' | 'role' | 'authOptions' | 'signingOrder'
+  'name' | 'email' | 'role' | 'authOptions' | 'signingOrder' | 'token'
 > & {
   templateRecipientId: number;
   fields: Field[];
@@ -351,6 +351,7 @@ export const createDocumentFromTemplate = async ({
       role: templateRecipient.role,
       signingOrder: foundRecipient?.signingOrder ?? templateRecipient.signingOrder,
       authOptions: templateRecipient.authOptions,
+      token: nanoid(),
     };
   });
 
@@ -451,7 +452,7 @@ export const createDocumentFromTemplate = async ({
                     ? SigningStatus.SIGNED
                     : SigningStatus.NOT_SIGNED,
                 signingOrder: recipient.signingOrder,
-                token: nanoid(),
+                token: recipient.token,
               };
             }),
           },
@@ -510,8 +511,8 @@ export const createDocumentFromTemplate = async ({
       }
     }
 
-    Object.values(finalRecipients).forEach(({ email, fields }) => {
-      const recipient = document.recipients.find((recipient) => recipient.email === email);
+    Object.values(finalRecipients).forEach(({ token, fields }) => {
+      const recipient = document.recipients.find((recipient) => recipient.token === token);
 
       if (!recipient) {
         throw new Error('Recipient not found.');

packages/lib/types/document-audit-logs.ts

@@ -41,6 +41,11 @@ export const ZDocumentAuditLogTypeSchema = z.enum([
   'DOCUMENT_EXTERNAL_ID_UPDATED', // When the document external ID is updated.
   'DOCUMENT_MOVED_TO_TEAM', // When the document is moved to a team.
   'DOCUMENT_ATTACHMENTS_UPDATED', // When the document attachments are updated.
+
+  // ACCESS AUTH 2FA events.
+  'DOCUMENT_ACCESS_AUTH_2FA_REQUESTED', // When ACCESS AUTH 2FA is requested.
+  'DOCUMENT_ACCESS_AUTH_2FA_VALIDATED', // When ACCESS AUTH 2FA is successfully validated.
+  'DOCUMENT_ACCESS_AUTH_2FA_FAILED', // When ACCESS AUTH 2FA validation fails.
 ]);
 
 export const ZDocumentAuditLogEmailTypeSchema = z.enum([
@@ -488,6 +493,42 @@ export const ZDocumentAuditLogEventDocumentRecipientRejectedSchema = z.object({
   }),
 });
 
+/**
+ * Event: Document recipient requested a 2FA token.
+ */
+export const ZDocumentAuditLogEventDocumentRecipientRequested2FAEmailSchema = z.object({
+  type: z.literal(DOCUMENT_AUDIT_LOG_TYPE.DOCUMENT_ACCESS_AUTH_2FA_REQUESTED),
+  data: z.object({
+    recipientEmail: z.string(),
+    recipientName: z.string(),
+    recipientId: z.number(),
+  }),
+});
+
+/**
+ * Event: Document recipient validated a 2FA token.
+ */
+export const ZDocumentAuditLogEventDocumentRecipientValidated2FAEmailSchema = z.object({
+  type: z.literal(DOCUMENT_AUDIT_LOG_TYPE.DOCUMENT_ACCESS_AUTH_2FA_VALIDATED),
+  data: z.object({
+    recipientEmail: z.string(),
+    recipientName: z.string(),
+    recipientId: z.number(),
+  }),
+});
+
+/**
+ * Event: Document recipient failed to validate a 2FA token.
+ */
+export const ZDocumentAuditLogEventDocumentRecipientFailed2FAEmailSchema = z.object({
+  type: z.literal(DOCUMENT_AUDIT_LOG_TYPE.DOCUMENT_ACCESS_AUTH_2FA_FAILED),
+  data: z.object({
+    recipientEmail: z.string(),
+    recipientName: z.string(),
+    recipientId: z.number(),
+  }),
+});
+
 /**
  * Event: Document sent.
  */
@@ -651,6 +692,9 @@ export const ZDocumentAuditLogSchema = ZDocumentAuditLogBaseSchema.and(
     ZDocumentAuditLogEventDocumentViewedSchema,
     ZDocumentAuditLogEventDocumentRecipientCompleteSchema,
     ZDocumentAuditLogEventDocumentRecipientRejectedSchema,
+    ZDocumentAuditLogEventDocumentRecipientRequested2FAEmailSchema,
+    ZDocumentAuditLogEventDocumentRecipientValidated2FAEmailSchema,
+    ZDocumentAuditLogEventDocumentRecipientFailed2FAEmailSchema,
     ZDocumentAuditLogEventDocumentSentSchema,
     ZDocumentAuditLogEventDocumentTitleUpdatedSchema,
     ZDocumentAuditLogEventDocumentExternalIdUpdatedSchema,

packages/lib/types/document-auth.ts

@@ -37,6 +37,7 @@ const ZDocumentAuthPasswordSchema = z.object({
 const ZDocumentAuth2FASchema = z.object({
   type: z.literal(DocumentAuth.TWO_FACTOR_AUTH),
   token: z.string().min(4).max(10),
+  method: z.enum(['email', 'authenticator']).default('authenticator').optional(),
 });
 
 /**
@@ -55,9 +56,12 @@ export const ZDocumentAuthMethodsSchema = z.discriminatedUnion('type', [
  *
  * Must keep these two in sync.
  */
-export const ZDocumentAccessAuthSchema = z.discriminatedUnion('type', [ZDocumentAuthAccountSchema]);
+export const ZDocumentAccessAuthSchema = z.discriminatedUnion('type', [
+  ZDocumentAuthAccountSchema,
+  ZDocumentAuth2FASchema,
+]);
 export const ZDocumentAccessAuthTypesSchema = z
-  .enum([DocumentAuth.ACCOUNT])
+  .enum([DocumentAuth.ACCOUNT, DocumentAuth.TWO_FACTOR_AUTH])
   .describe('The type of authentication required for the recipient to access the document.');
 
 /**
@@ -89,9 +93,10 @@ export const ZDocumentActionAuthTypesSchema = z
  */
 export const ZRecipientAccessAuthSchema = z.discriminatedUnion('type', [
   ZDocumentAuthAccountSchema,
+  ZDocumentAuth2FASchema,
 ]);
 export const ZRecipientAccessAuthTypesSchema = z
-  .enum([DocumentAuth.ACCOUNT])
+  .enum([DocumentAuth.ACCOUNT, DocumentAuth.TWO_FACTOR_AUTH])
   .describe('The type of authentication required for the recipient to access the document.');
 
 /**

packages/lib/utils/document-audit-logs.ts

@@ -476,6 +476,36 @@ export const formatDocumentAuditLogAction = (
         identified: result,
       };
     })
+    .with({ type: DOCUMENT_AUDIT_LOG_TYPE.DOCUMENT_ACCESS_AUTH_2FA_REQUESTED }, ({ data }) => {
+      const userName = prefix || _(msg`Recipient`);
+
+      const result = msg`${userName} requested a 2FA token for the document`;
+
+      return {
+        anonymous: result,
+        identified: result,
+      };
+    })
+    .with({ type: DOCUMENT_AUDIT_LOG_TYPE.DOCUMENT_ACCESS_AUTH_2FA_VALIDATED }, ({ data }) => {
+      const userName = prefix || _(msg`Recipient`);
+
+      const result = msg`${userName} validated a 2FA token for the document`;
+
+      return {
+        anonymous: result,
+        identified: result,
+      };
+    })
+    .with({ type: DOCUMENT_AUDIT_LOG_TYPE.DOCUMENT_ACCESS_AUTH_2FA_FAILED }, ({ data }) => {
+      const userName = prefix || _(msg`Recipient`);
+
+      const result = msg`${userName} failed to validate a 2FA token for the document`;
+
+      return {
+        anonymous: result,
+        identified: result,
+      };
+    })
     .with({ type: DOCUMENT_AUDIT_LOG_TYPE.EMAIL_SENT }, ({ data }) => ({
       anonymous: data.isResending ? msg`Email resent` : msg`Email sent`,
       identified: data.isResending

packages/prisma/migrations/20250917042725_remove_recipient_unique_email_constraints/migration.sql

@@ -0,0 +1,5 @@
+-- DropIndex
+DROP INDEX "Recipient_documentId_email_key";
+
+-- DropIndex
+DROP INDEX "Recipient_templateId_email_key";

packages/prisma/schema.prisma

@@ -554,8 +554,6 @@ model Recipient {
   fields            Field[]
   signatures        Signature[]
 
-  @@unique([documentId, email])
-  @@unique([templateId, email])
   @@index([documentId])
   @@index([templateId])
   @@index([token])

packages/trpc/server/admin-router/promote-member-to-owner.ts

@@ -0,0 +1,124 @@
+import { OrganisationGroupType, OrganisationMemberRole } from '@prisma/client';
+
+import { AppError, AppErrorCode } from '@documenso/lib/errors/app-error';
+import { generateDatabaseId } from '@documenso/lib/universal/id';
+import { getHighestOrganisationRoleInGroup } from '@documenso/lib/utils/organisations';
+import { prisma } from '@documenso/prisma';
+
+import { adminProcedure } from '../trpc';
+import {
+  ZPromoteMemberToOwnerRequestSchema,
+  ZPromoteMemberToOwnerResponseSchema,
+} from './promote-member-to-owner.types';
+
+export const promoteMemberToOwnerRoute = adminProcedure
+  .input(ZPromoteMemberToOwnerRequestSchema)
+  .output(ZPromoteMemberToOwnerResponseSchema)
+  .mutation(async ({ input, ctx }) => {
+    const { organisationId, userId } = input;
+
+    ctx.logger.info({
+      input: {
+        organisationId,
+        userId,
+      },
+    });
+
+    // First, verify the organisation exists and get member details with groups
+    const organisation = await prisma.organisation.findUnique({
+      where: {
+        id: organisationId,
+      },
+      include: {
+        groups: {
+          where: {
+            type: OrganisationGroupType.INTERNAL_ORGANISATION,
+          },
+        },
+        members: {
+          where: {
+            userId,
+          },
+          include: {
+            organisationGroupMembers: {
+              include: {
+                group: true,
+              },
+            },
+          },
+        },
+      },
+    });
+
+    if (!organisation) {
+      throw new AppError(AppErrorCode.NOT_FOUND, {
+        message: 'Organisation not found',
+      });
+    }
+
+    // Verify the user is a member of the organisation
+    const [member] = organisation.members;
+
+    if (!member) {
+      throw new AppError(AppErrorCode.NOT_FOUND, {
+        message: 'User is not a member of this organisation',
+      });
+    }
+
+    // Verify the user is not already the owner
+    if (organisation.ownerUserId === userId) {
+      throw new AppError(AppErrorCode.INVALID_REQUEST, {
+        message: 'User is already the owner of this organisation',
+      });
+    }
+
+    // Get current organisation role
+    const currentOrganisationRole = getHighestOrganisationRoleInGroup(
+      member.organisationGroupMembers.flatMap((member) => member.group),
+    );
+
+    // Find the current and target organisation groups
+    const currentMemberGroup = organisation.groups.find(
+      (group) => group.organisationRole === currentOrganisationRole,
+    );
+
+    const adminGroup = organisation.groups.find(
+      (group) => group.organisationRole === OrganisationMemberRole.ADMIN,
+    );
+
+    if (!currentMemberGroup) {
+      throw new AppError(AppErrorCode.UNKNOWN_ERROR, {
+        message: 'Current member group not found',
+      });
+    }
+
+    if (!adminGroup) {
+      throw new AppError(AppErrorCode.UNKNOWN_ERROR, {
+        message: 'Admin group not found',
+      });
+    }
+
+    // Update the organisation owner and member role in a transaction
+    await prisma.$transaction(async (tx) => {
+      // Update the organisation to set the new owner
+      await tx.organisation.update({
+        where: {
+          id: organisationId,
+        },
+        data: {
+          ownerUserId: userId,
+        },
+      });
+
+      // Only update role if the user is not already an admin then add them to the admin group
+      if (currentOrganisationRole !== OrganisationMemberRole.ADMIN) {
+        await tx.organisationGroupMember.create({
+          data: {
+            id: generateDatabaseId('group_member'),
+            organisationMemberId: member.id,
+            groupId: adminGroup.id,
+          },
+        });
+      }
+    });
+  });

packages/trpc/server/admin-router/promote-member-to-owner.types.ts

@@ -0,0 +1,11 @@
+import { z } from 'zod';
+
+export const ZPromoteMemberToOwnerRequestSchema = z.object({
+  organisationId: z.string().min(1),
+  userId: z.number().min(1),
+});
+
+export const ZPromoteMemberToOwnerResponseSchema = z.void();
+
+export type TPromoteMemberToOwnerRequest = z.infer<typeof ZPromoteMemberToOwnerRequestSchema>;
+export type TPromoteMemberToOwnerResponse = z.infer<typeof ZPromoteMemberToOwnerResponseSchema>;

packages/trpc/server/admin-router/router.ts

@@ -12,6 +12,7 @@ import { findDocumentsRoute } from './find-documents';
 import { findSubscriptionClaimsRoute } from './find-subscription-claims';
 import { getAdminOrganisationRoute } from './get-admin-organisation';
 import { getUserRoute } from './get-user';
+import { promoteMemberToOwnerRoute } from './promote-member-to-owner';
 import { resealDocumentRoute } from './reseal-document';
 import { resetTwoFactorRoute } from './reset-two-factor-authentication';
 import { updateAdminOrganisationRoute } from './update-admin-organisation';
@@ -27,6 +28,9 @@ export const adminRouter = router({
     create: createAdminOrganisationRoute,
     update: updateAdminOrganisationRoute,
   },
+  organisationMember: {
+    promoteToOwner: promoteMemberToOwnerRoute,
+  },
   claims: {
     find: findSubscriptionClaimsRoute,
     create: createSubscriptionClaimRoute,

packages/trpc/server/document-router/access-auth-request-2fa-email.ts

@@ -0,0 +1,94 @@
+import { TRPCError } from '@trpc/server';
+import { DateTime } from 'luxon';
+
+import { TWO_FACTOR_EMAIL_EXPIRATION_MINUTES } from '@documenso/lib/server-only/2fa/email/constants';
+import { send2FATokenEmail } from '@documenso/lib/server-only/2fa/email/send-2fa-token-email';
+import { DocumentAuth } from '@documenso/lib/types/document-auth';
+import { extractDocumentAuthMethods } from '@documenso/lib/utils/document-auth';
+import { prisma } from '@documenso/prisma';
+
+import { procedure } from '../trpc';
+import {
+  ZAccessAuthRequest2FAEmailRequestSchema,
+  ZAccessAuthRequest2FAEmailResponseSchema,
+} from './access-auth-request-2fa-email.types';
+
+export const accessAuthRequest2FAEmailRoute = procedure
+  .input(ZAccessAuthRequest2FAEmailRequestSchema)
+  .output(ZAccessAuthRequest2FAEmailResponseSchema)
+  .mutation(async ({ input, ctx }) => {
+    try {
+      const { token } = input;
+
+      const user = ctx.user;
+
+      // Get document and recipient by token
+      const document = await prisma.document.findFirst({
+        where: {
+          recipients: {
+            some: {
+              token,
+            },
+          },
+        },
+        include: {
+          recipients: {
+            where: {
+              token,
+            },
+          },
+        },
+      });
+
+      if (!document) {
+        throw new TRPCError({
+          code: 'NOT_FOUND',
+          message: 'Document not found',
+        });
+      }
+
+      const [recipient] = document.recipients;
+
+      const { derivedRecipientAccessAuth } = extractDocumentAuthMethods({
+        documentAuth: document.authOptions,
+        recipientAuth: recipient.authOptions,
+      });
+
+      if (!derivedRecipientAccessAuth.includes(DocumentAuth.TWO_FACTOR_AUTH)) {
+        throw new TRPCError({
+          code: 'BAD_REQUEST',
+          message: '2FA is not required for this document',
+        });
+      }
+
+      // if (user && recipient.email !== user.email) {
+      //   throw new TRPCError({
+      //     code: 'UNAUTHORIZED',
+      //     message: 'User does not match recipient',
+      //   });
+      // }
+
+      const expiresAt = DateTime.now().plus({ minutes: TWO_FACTOR_EMAIL_EXPIRATION_MINUTES });
+
+      await send2FATokenEmail({
+        token,
+        documentId: document.id,
+      });
+
+      return {
+        success: true,
+        expiresAt: expiresAt.toJSDate(),
+      };
+    } catch (error) {
+      console.error('Error sending access auth 2FA email:', error);
+
+      if (error instanceof TRPCError) {
+        throw error;
+      }
+
+      throw new TRPCError({
+        code: 'INTERNAL_SERVER_ERROR',
+        message: 'Failed to send 2FA email',
+      });
+    }
+  });

packages/trpc/server/document-router/access-auth-request-2fa-email.types.ts

@@ -0,0 +1,17 @@
+import { z } from 'zod';
+
+export const ZAccessAuthRequest2FAEmailRequestSchema = z.object({
+  token: z.string().min(1),
+});
+
+export const ZAccessAuthRequest2FAEmailResponseSchema = z.object({
+  success: z.boolean(),
+  expiresAt: z.date(),
+});
+
+export type TAccessAuthRequest2FAEmailRequest = z.infer<
+  typeof ZAccessAuthRequest2FAEmailRequestSchema
+>;
+export type TAccessAuthRequest2FAEmailResponse = z.infer<
+  typeof ZAccessAuthRequest2FAEmailResponseSchema
+>;

packages/trpc/server/document-router/create-document-temporary.types.ts

@@ -78,14 +78,7 @@ export const ZCreateDocumentTemporaryRequestSchema = z.object({
           .optional(),
       }),
     )
-    .refine(
-      (recipients) => {
-        const emails = recipients.map((recipient) => recipient.email);
 
-        return new Set(emails).size === emails.length;
-      },
-      { message: 'Recipients must have unique emails' },
-    )
     .optional(),
   meta: z
     .object({

packages/trpc/server/document-router/router.ts

@@ -1,4 +1,5 @@
 import { router } from '../trpc';
+import { accessAuthRequest2FAEmailRoute } from './access-auth-request-2fa-email';
 import { createDocumentRoute } from './create-document';
 import { createDocumentTemporaryRoute } from './create-document-temporary';
 import { deleteDocumentRoute } from './delete-document';
@@ -40,6 +41,10 @@ export const documentRouter = router({
   getDocumentByToken: getDocumentByTokenRoute,
   findDocumentsInternal: findDocumentsInternalRoute,
 
+  accessAuth: router({
+    request2FAEmail: accessAuthRequest2FAEmailRoute,
+  }),
+
   auditLog: {
     find: findDocumentAuditLogsRoute,
     download: downloadDocumentAuditLogsRoute,

packages/trpc/server/embedding-router/create-embedding-document.types.ts

@@ -47,14 +47,7 @@ export const ZCreateEmbeddingDocumentRequestSchema = z.object({
           .optional(),
       }),
     )
-    .refine(
-      (recipients) => {
-        const emails = recipients.map((recipient) => recipient.email);
 
-        return new Set(emails).size === emails.length;
-      },
-      { message: 'Recipients must have unique emails' },
-    )
     .optional(),
   meta: z
     .object({

packages/trpc/server/embedding-router/update-embedding-document.types.ts

@@ -30,36 +30,27 @@ export const ZUpdateEmbeddingDocumentRequestSchema = z.object({
   documentId: z.number(),
   title: ZDocumentTitleSchema,
   externalId: ZDocumentExternalIdSchema.optional(),
-  recipients: z
-    .array(
-      z.object({
-        id: z.number().optional(),
-        email: z.string().toLowerCase().email().min(1),
-        name: z.string(),
-        role: z.nativeEnum(RecipientRole),
-        signingOrder: z.number().optional(),
-        fields: ZFieldAndMetaSchema.and(
-          z.object({
-            id: z.number().optional(),
-            pageNumber: ZFieldPageNumberSchema,
-            pageX: ZFieldPageXSchema,
-            pageY: ZFieldPageYSchema,
-            width: ZFieldWidthSchema,
-            height: ZFieldHeightSchema,
-          }),
-        )
-          .array()
-          .optional(),
-      }),
-    )
-    .refine(
-      (recipients) => {
-        const emails = recipients.map((recipient) => recipient.email);
-
-        return new Set(emails).size === emails.length;
-      },
-      { message: 'Recipients must have unique emails' },
-    ),
+  recipients: z.array(
+    z.object({
+      id: z.number().optional(),
+      email: z.string().toLowerCase().email().min(1),
+      name: z.string(),
+      role: z.nativeEnum(RecipientRole),
+      signingOrder: z.number().optional(),
+      fields: ZFieldAndMetaSchema.and(
+        z.object({
+          id: z.number().optional(),
+          pageNumber: ZFieldPageNumberSchema,
+          pageX: ZFieldPageXSchema,
+          pageY: ZFieldPageYSchema,
+          width: ZFieldWidthSchema,
+          height: ZFieldHeightSchema,
+        }),
+      )
+        .array()
+        .optional(),
+    }),
+  ),
   meta: z
     .object({
       subject: ZDocumentMetaSubjectSchema.optional(),

packages/trpc/server/field-router/router.ts

@@ -274,6 +274,7 @@ export const fieldRouter = router({
         fields: fields.map((field) => ({
           id: field.nativeId,
           signerEmail: field.signerEmail,
+          recipientId: field.recipientId,
           type: field.type,
           pageNumber: field.pageNumber,
           pageX: field.pageX,
@@ -513,6 +514,7 @@ export const fieldRouter = router({
         fields: fields.map((field) => ({
           id: field.nativeId,
           signerEmail: field.signerEmail,
+          recipientId: field.recipientId,
           type: field.type,
           pageNumber: field.pageNumber,
           pageX: field.pageX,

packages/trpc/server/field-router/schema.ts

@@ -114,6 +114,7 @@ export const ZSetDocumentFieldsRequestSchema = z.object({
       nativeId: z.number().optional(),
       type: z.nativeEnum(FieldType),
       signerEmail: z.string().min(1),
+      recipientId: z.number().min(1),
       pageNumber: z.number().min(1),
       pageX: z.number().min(0),
       pageY: z.number().min(0),
@@ -136,6 +137,7 @@ export const ZSetFieldsForTemplateRequestSchema = z.object({
       nativeId: z.number().optional(),
       type: z.nativeEnum(FieldType),
       signerEmail: z.string().min(1),
+      recipientId: z.number().min(1),
       pageNumber: z.number().min(1),
       pageX: z.number().min(0),
       pageY: z.number().min(0),

packages/trpc/server/organisation-router/update-organisation-settings.ts

@@ -1,3 +1,5 @@
+import { OrganisationType } from '@prisma/client';
+
 import { ORGANISATION_MEMBER_ROLE_PERMISSIONS_MAP } from '@documenso/lib/constants/organisations';
 import { AppError, AppErrorCode } from '@documenso/lib/errors/app-error';
 import { buildOrganisationWhereQuery } from '@documenso/lib/utils/organisations';
@@ -104,6 +106,19 @@ export const updateOrganisationSettingsRoute = authenticatedProcedure
       });
     }
 
+    const isPersonalOrganisation = organisation.type === OrganisationType.PERSONAL;
+    const currentIncludeSenderDetails =
+      organisation.organisationGlobalSettings.includeSenderDetails;
+
+    const isChangingIncludeSenderDetails =
+      includeSenderDetails !== undefined && includeSenderDetails !== currentIncludeSenderDetails;
+
+    if (isPersonalOrganisation && isChangingIncludeSenderDetails) {
+      throw new AppError(AppErrorCode.INVALID_BODY, {
+        message: 'Personal organisations cannot update the sender details',
+      });
+    }
+
     await prisma.organisation.update({
       where: {
         id: organisationId,

packages/trpc/server/recipient-router/router.ts

@@ -525,7 +525,7 @@ export const recipientRouter = router({
   completeDocumentWithToken: procedure
     .input(ZCompleteDocumentWithTokenMutationSchema)
     .mutation(async ({ input, ctx }) => {
-      const { token, documentId, authOptions, nextSigner } = input;
+      const { token, documentId, authOptions, accessAuthOptions, nextSigner } = input;
 
       ctx.logger.info({
         input: {
@@ -537,6 +537,7 @@ export const recipientRouter = router({
         token,
         documentId,
         authOptions,
+        accessAuthOptions,
         nextSigner,
         userId: ctx.user?.id,
         requestMetadata: ctx.metadata.requestMetadata,

packages/trpc/server/recipient-router/schema.ts

@@ -3,6 +3,7 @@ import { z } from 'zod';
 
 import { isTemplateRecipientEmailPlaceholder } from '@documenso/lib/constants/template';
 import {
+  ZRecipientAccessAuthSchema,
   ZRecipientAccessAuthTypesSchema,
   ZRecipientActionAuthSchema,
   ZRecipientActionAuthTypesSchema,
@@ -50,16 +51,7 @@ export const ZCreateDocumentRecipientResponseSchema = ZRecipientLiteSchema;
 
 export const ZCreateDocumentRecipientsRequestSchema = z.object({
   documentId: z.number(),
-  recipients: z.array(ZCreateRecipientSchema).refine(
-    (recipients) => {
-      const emails = recipients.map((recipient) => recipient.email.toLowerCase());
-
-      return new Set(emails).size === emails.length;
-    },
-    {
-      message: 'Recipients must have unique emails',
-    },
-  ),
+  recipients: z.array(ZCreateRecipientSchema),
 });
 
 export const ZCreateDocumentRecipientsResponseSchema = z.object({
@@ -75,18 +67,7 @@ export const ZUpdateDocumentRecipientResponseSchema = ZRecipientSchema;
 
 export const ZUpdateDocumentRecipientsRequestSchema = z.object({
   documentId: z.number(),
-  recipients: z.array(ZUpdateRecipientSchema).refine(
-    (recipients) => {
-      const emails = recipients
-        .filter((recipient) => recipient.email !== undefined)
-        .map((recipient) => recipient.email?.toLowerCase());
-
-      return new Set(emails).size === emails.length;
-    },
-    {
-      message: 'Recipients must have unique emails',
-    },
-  ),
+  recipients: z.array(ZUpdateRecipientSchema),
 });
 
 export const ZUpdateDocumentRecipientsResponseSchema = z.object({
@@ -97,29 +78,19 @@ export const ZDeleteDocumentRecipientRequestSchema = z.object({
   recipientId: z.number(),
 });
 
-export const ZSetDocumentRecipientsRequestSchema = z
-  .object({
-    documentId: z.number(),
-    recipients: z.array(
-      z.object({
-        nativeId: z.number().optional(),
-        email: z.string().toLowerCase().email().min(1).max(254),
-        name: z.string().max(255),
-        role: z.nativeEnum(RecipientRole),
-        signingOrder: z.number().optional(),
-        actionAuth: z.array(ZRecipientActionAuthTypesSchema).optional().default([]),
-      }),
-    ),
-  })
-  .refine(
-    (schema) => {
-      const emails = schema.recipients.map((recipient) => recipient.email.toLowerCase());
-
-      return new Set(emails).size === emails.length;
-    },
-    // Dirty hack to handle errors when .root is populated for an array type
-    { message: 'Recipients must have unique emails', path: ['recipients__root'] },
-  );
+export const ZSetDocumentRecipientsRequestSchema = z.object({
+  documentId: z.number(),
+  recipients: z.array(
+    z.object({
+      nativeId: z.number().optional(),
+      email: z.string().toLowerCase().email().min(1).max(254),
+      name: z.string().max(255),
+      role: z.nativeEnum(RecipientRole),
+      signingOrder: z.number().optional(),
+      actionAuth: z.array(ZRecipientActionAuthTypesSchema).optional().default([]),
+    }),
+  ),
+});
 
 export const ZSetDocumentRecipientsResponseSchema = z.object({
   recipients: ZRecipientLiteSchema.array(),
@@ -134,16 +105,7 @@ export const ZCreateTemplateRecipientResponseSchema = ZRecipientLiteSchema;
 
 export const ZCreateTemplateRecipientsRequestSchema = z.object({
   templateId: z.number(),
-  recipients: z.array(ZCreateRecipientSchema).refine(
-    (recipients) => {
-      const emails = recipients.map((recipient) => recipient.email);
-
-      return new Set(emails).size === emails.length;
-    },
-    {
-      message: 'Recipients must have unique emails',
-    },
-  ),
+  recipients: z.array(ZCreateRecipientSchema),
 });
 
 export const ZCreateTemplateRecipientsResponseSchema = z.object({
@@ -159,18 +121,7 @@ export const ZUpdateTemplateRecipientResponseSchema = ZRecipientSchema;
 
 export const ZUpdateTemplateRecipientsRequestSchema = z.object({
   templateId: z.number(),
-  recipients: z.array(ZUpdateRecipientSchema).refine(
-    (recipients) => {
-      const emails = recipients
-        .filter((recipient) => recipient.email !== undefined)
-        .map((recipient) => recipient.email);
-
-      return new Set(emails).size === emails.length;
-    },
-    {
-      message: 'Recipients must have unique emails',
-    },
-  ),
+  recipients: z.array(ZUpdateRecipientSchema),
 });
 
 export const ZUpdateTemplateRecipientsResponseSchema = z.object({
@@ -181,43 +132,30 @@ export const ZDeleteTemplateRecipientRequestSchema = z.object({
   recipientId: z.number(),
 });
 
-export const ZSetTemplateRecipientsRequestSchema = z
-  .object({
-    templateId: z.number(),
-    recipients: z.array(
-      z.object({
-        nativeId: z.number().optional(),
-        email: z
-          .string()
-          .toLowerCase()
-          .refine(
-            (email) => {
-              return (
-                isTemplateRecipientEmailPlaceholder(email) ||
-                z.string().email().safeParse(email).success
-              );
-            },
-            { message: 'Please enter a valid email address' },
-          ),
-        name: z.string(),
-        role: z.nativeEnum(RecipientRole),
-        signingOrder: z.number().optional(),
-        actionAuth: z.array(ZRecipientActionAuthTypesSchema).optional().default([]),
-      }),
-    ),
-  })
-  .refine(
-    (schema) => {
-      // Filter out placeholder emails and only check uniqueness for actual emails
-      const nonPlaceholderEmails = schema.recipients
-        .map((recipient) => recipient.email)
-        .filter((email) => !isTemplateRecipientEmailPlaceholder(email));
-
-      return new Set(nonPlaceholderEmails).size === nonPlaceholderEmails.length;
-    },
-    // Dirty hack to handle errors when .root is populated for an array type
-    { message: 'Recipients must have unique emails', path: ['recipients__root'] },
-  );
+export const ZSetTemplateRecipientsRequestSchema = z.object({
+  templateId: z.number(),
+  recipients: z.array(
+    z.object({
+      nativeId: z.number().optional(),
+      email: z
+        .string()
+        .toLowerCase()
+        .refine(
+          (email) => {
+            return (
+              isTemplateRecipientEmailPlaceholder(email) ||
+              z.string().email().safeParse(email).success
+            );
+          },
+          { message: 'Please enter a valid email address' },
+        ),
+      name: z.string(),
+      role: z.nativeEnum(RecipientRole),
+      signingOrder: z.number().optional(),
+      actionAuth: z.array(ZRecipientActionAuthTypesSchema).optional().default([]),
+    }),
+  ),
+});
 
 export const ZSetTemplateRecipientsResponseSchema = z.object({
   recipients: ZRecipientLiteSchema.array(),
@@ -227,6 +165,7 @@ export const ZCompleteDocumentWithTokenMutationSchema = z.object({
   token: z.string(),
   documentId: z.number(),
   authOptions: ZRecipientActionAuthSchema.optional(),
+  accessAuthOptions: ZRecipientAccessAuthSchema.optional(),
   nextSigner: z
     .object({
       email: z.string().email().max(254),

packages/trpc/server/team-router/update-team-settings.ts

@@ -1,7 +1,10 @@
 import { Prisma } from '@prisma/client';
+import { OrganisationType } from '@prisma/client';
 
+import { ORGANISATION_MEMBER_ROLE_PERMISSIONS_MAP } from '@documenso/lib/constants/organisations';
 import { TEAM_MEMBER_ROLE_PERMISSIONS_MAP } from '@documenso/lib/constants/teams';
 import { AppError, AppErrorCode } from '@documenso/lib/errors/app-error';
+import { buildOrganisationWhereQuery } from '@documenso/lib/utils/organisations';
 import { buildTeamWhereQuery } from '@documenso/lib/utils/teams';
 import { prisma } from '@documenso/prisma';
 
@@ -97,6 +100,35 @@ export const updateTeamSettingsRoute = authenticatedProcedure
       }
     }
 
+    const organisation = await prisma.organisation.findFirst({
+      where: buildOrganisationWhereQuery({
+        organisationId: team.organisationId,
+        userId: user.id,
+        roles: ORGANISATION_MEMBER_ROLE_PERMISSIONS_MAP['MANAGE_ORGANISATION'],
+      }),
+      select: {
+        type: true,
+        organisationGlobalSettings: {
+          select: {
+            includeSenderDetails: true,
+          },
+        },
+      },
+    });
+
+    const isPersonalOrganisation = organisation?.type === OrganisationType.PERSONAL;
+    const currentIncludeSenderDetails =
+      organisation?.organisationGlobalSettings.includeSenderDetails;
+
+    const isChangingIncludeSenderDetails =
+      includeSenderDetails !== undefined && includeSenderDetails !== currentIncludeSenderDetails;
+
+    if (isPersonalOrganisation && isChangingIncludeSenderDetails) {
+      throw new AppError(AppErrorCode.INVALID_BODY, {
+        message: 'Personal teams cannot update the sender details',
+      });
+    }
+
     await prisma.team.update({
       where: {
         id: teamId,

packages/trpc/server/template-router/schema.ts

@@ -101,12 +101,7 @@ export const ZCreateDocumentFromTemplateRequestSchema = z.object({
         name: z.string().max(255).optional(),
       }),
     )
-    .describe('The information of the recipients to create the document with.')
-    .refine((recipients) => {
-      const emails = recipients.map((signer) => signer.email);
-
-      return new Set(emails).size === emails.length;
-    }, 'Recipients must have unique emails'),
+    .describe('The information of the recipients to create the document with.'),
   distributeDocument: z
     .boolean()
     .describe('Whether to create the document as pending and distribute it to recipients.')

packages/ui/components/document/document-read-only-fields.tsx

@@ -105,6 +105,7 @@ export const DocumentReadOnlyFields = ({
             <FieldRootContainer
               field={field}
               key={field.id}
+              readonly={true}
               color={
                 showRecipientColors
                   ? getRecipientColorStyles(

packages/ui/components/field/field.tsx

@@ -70,9 +70,16 @@ export type FieldRootContainerProps = {
   color?: RecipientColorStyles;
   children: React.ReactNode;
   className?: string;
+  readonly?: boolean;
 };
 
-export function FieldRootContainer({ field, children, color, className }: FieldRootContainerProps) {
+export function FieldRootContainer({
+  field,
+  children,
+  color,
+  className,
+  readonly,
+}: FieldRootContainerProps) {
   const [isValidating, setIsValidating] = useState(false);
   const ref = React.useRef<HTMLDivElement>(null);
 
@@ -103,6 +110,7 @@ export function FieldRootContainer({ field, children, color, className }: FieldR
         ref={ref}
         data-field-type={field.type}
         data-inserted={field.inserted ? 'true' : 'false'}
+        data-readonly={readonly ? 'true' : 'false'}
         className={cn(
           'field--FieldRootContainer field-card-container dark-mode-disabled group relative z-20 flex h-full w-full items-center rounded-[2px] bg-white/90 ring-2 ring-gray-200 transition-all',
           color?.base,

packages/ui/primitives/badge.tsx

@@ -39,7 +39,9 @@ export interface BadgeProps
     VariantProps<typeof badgeVariants> {}
 
 function Badge({ className, variant, size, ...props }: BadgeProps) {
-  return <div className={cn(badgeVariants({ variant, size }), className)} {...props} />;
+  return (
+    <div role="status" className={cn(badgeVariants({ variant, size }), className)} {...props} />
+  );
 }
 
 export { Badge, badgeVariants };

packages/ui/primitives/document-flow/add-fields.tsx

@@ -1,5 +1,6 @@
 import { useCallback, useEffect, useMemo, useRef, useState } from 'react';
 
+import { zodResolver } from '@hookform/resolvers/zod';
 import { msg } from '@lingui/core/macro';
 import { useLingui } from '@lingui/react';
 import { Trans } from '@lingui/react/macro';
@@ -46,7 +47,7 @@ import { Form } from '../form/form';
 import { RecipientSelector } from '../recipient-selector';
 import { useStep } from '../stepper';
 import { useToast } from '../use-toast';
-import type { TAddFieldsFormSchema } from './add-fields.types';
+import { type TAddFieldsFormSchema, ZAddFieldsFormSchema } from './add-fields.types';
 import {
   DocumentFlowFormContainerActions,
   DocumentFlowFormContainerContent,
@@ -75,6 +76,7 @@ export type FieldFormType = {
   pageWidth: number;
   pageHeight: number;
   signerEmail: string;
+  recipientId: number;
   fieldMeta?: FieldMeta;
 };
 
@@ -127,9 +129,11 @@ export const AddFieldsFormPartial = ({
         pageHeight: Number(field.height),
         signerEmail:
           recipients.find((recipient) => recipient.id === field.recipientId)?.email ?? '',
+        recipientId: field.recipientId,
         fieldMeta: field.fieldMeta ? ZFieldMetaSchema.parse(field.fieldMeta) : undefined,
       })),
     },
+    resolver: zodResolver(ZAddFieldsFormSchema),
   });
 
   useHotkeys(['ctrl+c', 'meta+c'], (evt) => onFieldCopy(evt));
@@ -323,6 +327,7 @@ export const AddFieldsFormPartial = ({
 
       const field = {
         formId: nanoid(12),
+        nativeId: undefined,
         type: selectedField,
         pageNumber,
         pageX,
@@ -330,6 +335,7 @@ export const AddFieldsFormPartial = ({
         pageWidth: fieldPageWidth,
         pageHeight: fieldPageHeight,
         signerEmail: selectedSigner.email,
+        recipientId: selectedSigner.id,
         fieldMeta: undefined,
       };
 
@@ -414,6 +420,7 @@ export const AddFieldsFormPartial = ({
             nativeId: undefined,
             formId: nanoid(12),
             signerEmail: selectedSigner?.email ?? lastActiveField.signerEmail,
+            recipientId: selectedSigner?.id ?? lastActiveField.recipientId,
             pageX: lastActiveField.pageX + 3,
             pageY: lastActiveField.pageY + 3,
           };
@@ -438,6 +445,7 @@ export const AddFieldsFormPartial = ({
               nativeId: undefined,
               formId: nanoid(12),
               signerEmail: selectedSigner?.email ?? lastActiveField.signerEmail,
+              recipientId: selectedSigner?.id ?? lastActiveField.recipientId,
               pageNumber,
             };
 
@@ -470,6 +478,7 @@ export const AddFieldsFormPartial = ({
           nativeId: undefined,
           formId: nanoid(12),
           signerEmail: selectedSigner?.email ?? copiedField.signerEmail,
+          recipientId: selectedSigner?.id ?? copiedField.recipientId,
           pageX: copiedField.pageX + 3,
           pageY: copiedField.pageY + 3,
         });
@@ -663,7 +672,7 @@ export const AddFieldsFormPartial = ({
 
               {isDocumentPdfLoaded &&
                 localFields.map((field, index) => {
-                  const recipientIndex = recipients.findIndex((r) => r.email === field.signerEmail);
+                  const recipientIndex = recipients.findIndex((r) => r.id === field.recipientId);
                   const hasFieldError =
                     emptyCheckboxFields.find((f) => f.formId === field.formId) ||
                     emptyRadioFields.find((f) => f.formId === field.formId) ||

packages/ui/primitives/document-flow/add-fields.types.ts

@@ -10,6 +10,7 @@ export const ZAddFieldsFormSchema = z.object({
       nativeId: z.number().optional(),
       type: z.nativeEnum(FieldType),
       signerEmail: z.string().min(1),
+      recipientId: z.number().min(1),
       pageNumber: z.number().min(1),
       pageX: z.number().min(0),
       pageY: z.number().min(0),

packages/ui/primitives/document-flow/add-signers.tsx

@@ -53,6 +53,10 @@ import {
 import { SigningOrderConfirmation } from './signing-order-confirmation';
 import type { DocumentFlowStep } from './types';
 
+type AutoSaveResponse = {
+  recipients: Recipient[];
+};
+
 export type AddSignersFormProps = {
   documentFlow: DocumentFlowStep;
   recipients: Recipient[];
@@ -60,7 +64,7 @@ export type AddSignersFormProps = {
   signingOrder?: DocumentSigningOrder | null;
   allowDictateNextSigner?: boolean;
   onSubmit: (_data: TAddSignersFormSchema) => void;
-  onAutoSave: (_data: TAddSignersFormSchema) => Promise<void>;
+  onAutoSave: (_data: TAddSignersFormSchema) => Promise<AutoSaveResponse>;
   isDocumentPdfLoaded: boolean;
 };
 
@@ -208,7 +212,44 @@ export const AddSignersFormPartial = ({
 
     const formData = form.getValues();
 
-    scheduleSave(formData);
+    scheduleSave(formData, (response) => {
+      // Sync the response recipients back to form state to prevent duplicates
+      if (response?.recipients) {
+        const currentSigners = form.getValues('signers');
+        const updatedSigners = currentSigners.map((signer) => {
+          // Find the matching recipient from the response using nativeId
+          const matchingRecipient = response.recipients.find(
+            (recipient) => recipient.id === signer.nativeId,
+          );
+
+          if (matchingRecipient) {
+            // Update the signer with the server-returned data, especially the ID
+            return {
+              ...signer,
+              nativeId: matchingRecipient.id,
+            };
+          }
+
+          // For new signers without nativeId, match by email and update with server ID
+          if (!signer.nativeId) {
+            const newRecipient = response.recipients.find(
+              (recipient) => recipient.email === signer.email,
+            );
+            if (newRecipient) {
+              return {
+                ...signer,
+                nativeId: newRecipient.id,
+              };
+            }
+          }
+
+          return signer;
+        });
+
+        // Update the form state with the synced data
+        form.setValue('signers', updatedSigners, { shouldValidate: false });
+      }
+    });
   };
 
   const emptySignerIndex = watchedSigners.findIndex((signer) => !signer.name && !signer.email);
@@ -714,7 +755,6 @@ export const AddSignersFormPartial = ({
                                           handleRecipientAutoCompleteSelect(index, suggestion)
                                         }
                                         onSearchQueryChange={(query) => {
-                                          console.log('onSearchQueryChange', query);
                                           field.onChange(query);
                                           setRecipientSearchQuery(query);
                                         }}

packages/ui/primitives/document-flow/add-signers.types.ts

@@ -4,33 +4,23 @@ import { z } from 'zod';
 
 import { ZRecipientActionAuthTypesSchema } from '@documenso/lib/types/document-auth';
 
-export const ZAddSignersFormSchema = z
-  .object({
-    signers: z.array(
-      z.object({
-        formId: z.string().min(1),
-        nativeId: z.number().optional(),
-        email: z
-          .string()
-          .email({ message: msg`Invalid email`.id })
-          .min(1),
-        name: z.string(),
-        role: z.nativeEnum(RecipientRole),
-        signingOrder: z.number().optional(),
-        actionAuth: z.array(ZRecipientActionAuthTypesSchema).optional().default([]),
-      }),
-    ),
-    signingOrder: z.nativeEnum(DocumentSigningOrder),
-    allowDictateNextSigner: z.boolean().default(false),
-  })
-  .refine(
-    (schema) => {
-      const emails = schema.signers.map((signer) => signer.email.toLowerCase());
-
-      return new Set(emails).size === emails.length;
-    },
-    // Dirty hack to handle errors when .root is populated for an array type
-    { message: msg`Signers must have unique emails`.id, path: ['signers__root'] },
-  );
+export const ZAddSignersFormSchema = z.object({
+  signers: z.array(
+    z.object({
+      formId: z.string().min(1),
+      nativeId: z.number().optional(),
+      email: z
+        .string()
+        .email({ message: msg`Invalid email`.id })
+        .min(1),
+      name: z.string(),
+      role: z.nativeEnum(RecipientRole),
+      signingOrder: z.number().optional(),
+      actionAuth: z.array(ZRecipientActionAuthTypesSchema).optional().default([]),
+    }),
+  ),
+  signingOrder: z.nativeEnum(DocumentSigningOrder),
+  allowDictateNextSigner: z.boolean().default(false),
+});
 
 export type TAddSignersFormSchema = z.infer<typeof ZAddSignersFormSchema>;

packages/ui/primitives/document-flow/field-item.tsx

@@ -299,6 +299,8 @@ export const FieldItem = ({
         }}
         ref={$el}
         data-field-id={field.nativeId}
+        data-field-type={field.type}
+        data-recipient-id={field.recipientId}
       >
         <FieldContent field={field} />
 

packages/ui/primitives/document-flow/types.ts

@@ -8,19 +8,14 @@ import { ZFieldMetaSchema } from '@documenso/lib/types/field-meta';
 export const ZDocumentFlowFormSchema = z.object({
   title: z.string().min(1),
 
-  signers: z
-    .array(
-      z.object({
-        formId: z.string().min(1),
-        nativeId: z.number().optional(),
-        email: z.string().min(1).email(),
-        name: z.string(),
-      }),
-    )
-    .refine((signers) => {
-      const emails = signers.map((signer) => signer.email);
-      return new Set(emails).size === emails.length;
-    }, 'Signers must have unique emails'),
+  signers: z.array(
+    z.object({
+      formId: z.string().min(1),
+      nativeId: z.number().optional(),
+      email: z.string().min(1).email(),
+      name: z.string(),
+    }),
+  ),
 
   fields: z.array(
     z.object({
@@ -28,6 +23,7 @@ export const ZDocumentFlowFormSchema = z.object({
       nativeId: z.number().optional(),
       type: z.nativeEnum(FieldType),
       signerEmail: z.string().min(1).optional(),
+      recipientId: z.number().min(1),
       pageNumber: z.number().min(1),
       pageX: z.number().min(0),
       pageY: z.number().min(0),

packages/ui/primitives/template-flow/add-template-fields.tsx

@@ -1,5 +1,6 @@
 import { useCallback, useEffect, useMemo, useRef, useState } from 'react';
 
+import { zodResolver } from '@hookform/resolvers/zod';
 import { msg } from '@lingui/core/macro';
 import { useLingui } from '@lingui/react';
 import { Trans } from '@lingui/react/macro';
@@ -61,7 +62,10 @@ import type { FieldFormType } from '../document-flow/add-fields';
 import { FieldAdvancedSettings } from '../document-flow/field-item-advanced-settings';
 import { Form } from '../form/form';
 import { useStep } from '../stepper';
-import type { TAddTemplateFieldsFormSchema } from './add-template-fields.types';
+import {
+  type TAddTemplateFieldsFormSchema,
+  ZAddTemplateFieldsFormSchema,
+} from './add-template-fields.types';
 
 const MIN_HEIGHT_PX = 12;
 const MIN_WIDTH_PX = 36;
@@ -112,7 +116,7 @@ export const AddTemplateFieldsFormPartial = ({
         pageY: Number(field.positionY),
         pageWidth: Number(field.width),
         pageHeight: Number(field.height),
-        signerId: field.recipientId ?? -1,
+        recipientId: field.recipientId ?? -1,
         signerEmail:
           recipients.find((recipient) => recipient.id === field.recipientId)?.email ?? '',
         signerToken:
@@ -120,6 +124,7 @@ export const AddTemplateFieldsFormPartial = ({
         fieldMeta: field.fieldMeta ? ZFieldMetaSchema.parse(field.fieldMeta) : undefined,
       })),
     },
+    resolver: zodResolver(ZAddTemplateFieldsFormSchema),
   });
 
   const onFormSubmit = form.handleSubmit(onSubmit);
@@ -170,7 +175,7 @@ export const AddTemplateFieldsFormPartial = ({
             nativeId: undefined,
             formId: nanoid(12),
             signerEmail: selectedSigner?.email ?? lastActiveField.signerEmail,
-            signerId: selectedSigner?.id ?? lastActiveField.signerId,
+            recipientId: selectedSigner?.id ?? lastActiveField.recipientId,
             signerToken: selectedSigner?.token ?? lastActiveField.signerToken,
             pageX: lastActiveField.pageX + 3,
             pageY: lastActiveField.pageY + 3,
@@ -197,7 +202,7 @@ export const AddTemplateFieldsFormPartial = ({
               nativeId: undefined,
               formId: nanoid(12),
               signerEmail: selectedSigner?.email ?? lastActiveField.signerEmail,
-              signerId: selectedSigner?.id ?? lastActiveField.signerId,
+              recipientId: selectedSigner?.id ?? lastActiveField.recipientId,
               signerToken: selectedSigner?.token ?? lastActiveField.signerToken,
               pageNumber,
             };
@@ -240,7 +245,7 @@ export const AddTemplateFieldsFormPartial = ({
           formId: nanoid(12),
           nativeId: undefined,
           signerEmail: selectedSigner?.email ?? copiedField.signerEmail,
-          signerId: selectedSigner?.id ?? copiedField.signerId,
+          recipientId: selectedSigner?.id ?? copiedField.recipientId,
           signerToken: selectedSigner?.token ?? copiedField.signerToken,
           pageX: copiedField.pageX + 3,
           pageY: copiedField.pageY + 3,
@@ -371,7 +376,7 @@ export const AddTemplateFieldsFormPartial = ({
         pageWidth: fieldPageWidth,
         pageHeight: fieldPageHeight,
         signerEmail: selectedSigner.email,
-        signerId: selectedSigner.id,
+        recipientId: selectedSigner.id,
         signerToken: selectedSigner.token ?? '',
         fieldMeta: undefined,
       };
@@ -597,14 +602,14 @@ export const AddTemplateFieldsFormPartial = ({
               )}
 
               {localFields.map((field, index) => {
-                const recipientIndex = recipients.findIndex((r) => r.email === field.signerEmail);
+                const recipientIndex = recipients.findIndex((r) => r.id === field.recipientId);
 
                 return (
                   <FieldItem
                     key={index}
                     recipientIndex={recipientIndex === -1 ? 0 : recipientIndex}
                     field={field}
-                    disabled={selectedSigner?.email !== field.signerEmail}
+                    disabled={selectedSigner?.id !== field.recipientId}
                     minHeight={MIN_HEIGHT_PX}
                     minWidth={MIN_WIDTH_PX}
                     defaultHeight={DEFAULT_HEIGHT_PX}

packages/ui/primitives/template-flow/add-template-fields.types.ts

@@ -10,8 +10,8 @@ export const ZAddTemplateFieldsFormSchema = z.object({
       nativeId: z.number().optional(),
       type: z.nativeEnum(FieldType),
       signerEmail: z.string().min(1),
+      recipientId: z.number().min(1),
       signerToken: z.string(),
-      signerId: z.number().optional(),
       pageNumber: z.number().min(1),
       pageX: z.number().min(0),
       pageY: z.number().min(0),

packages/ui/primitives/template-flow/add-template-placeholder-recipients.tsx

@@ -48,6 +48,10 @@ import { Tooltip, TooltipContent, TooltipTrigger } from '../tooltip';
 import type { TAddTemplatePlacholderRecipientsFormSchema } from './add-template-placeholder-recipients.types';
 import { ZAddTemplatePlacholderRecipientsFormSchema } from './add-template-placeholder-recipients.types';
 
+type AutoSaveResponse = {
+  recipients: Recipient[];
+};
+
 export type AddTemplatePlaceholderRecipientsFormProps = {
   documentFlow: DocumentFlowStep;
   recipients: Recipient[];
@@ -56,7 +60,7 @@ export type AddTemplatePlaceholderRecipientsFormProps = {
   allowDictateNextSigner?: boolean;
   templateDirectLink?: TemplateDirectLink | null;
   onSubmit: (_data: TAddTemplatePlacholderRecipientsFormSchema) => void;
-  onAutoSave: (_data: TAddTemplatePlacholderRecipientsFormSchema) => Promise<void>;
+  onAutoSave: (_data: TAddTemplatePlacholderRecipientsFormSchema) => Promise<AutoSaveResponse>;
   isDocumentPdfLoaded: boolean;
 };
 
@@ -146,7 +150,44 @@ export const AddTemplatePlaceholderRecipientsFormPartial = ({
 
     const formData = form.getValues();
 
-    scheduleSave(formData);
+    scheduleSave(formData, (response) => {
+      // Sync the response recipients back to form state to prevent duplicates
+      if (response?.recipients) {
+        const currentSigners = form.getValues('signers');
+        const updatedSigners = currentSigners.map((signer) => {
+          // Find the matching recipient from the response using nativeId
+          const matchingRecipient = response.recipients.find(
+            (recipient) => recipient.id === signer.nativeId,
+          );
+
+          if (matchingRecipient) {
+            // Update the signer with the server-returned data, especially the ID
+            return {
+              ...signer,
+              nativeId: matchingRecipient.id,
+            };
+          }
+
+          // For new signers without nativeId, match by email and update with server ID
+          if (!signer.nativeId) {
+            const newRecipient = response.recipients.find(
+              (recipient) => recipient.email === signer.email,
+            );
+            if (newRecipient) {
+              return {
+                ...signer,
+                nativeId: newRecipient.id,
+              };
+            }
+          }
+
+          return signer;
+        });
+
+        // Update the form state with the synced data
+        form.setValue('signers', updatedSigners, { shouldValidate: false });
+      }
+    });
   };
 
   // useEffect(() => {

packages/ui/primitives/template-flow/add-template-placeholder-recipients.types.ts

@@ -1,7 +1,6 @@
 import { DocumentSigningOrder, RecipientRole } from '@prisma/client';
 import { z } from 'zod';
 
-import { TEMPLATE_RECIPIENT_EMAIL_PLACEHOLDER_REGEX } from '@documenso/lib/constants/template';
 import { ZRecipientActionAuthTypesSchema } from '@documenso/lib/types/document-auth';
 
 export const ZAddTemplatePlacholderRecipientsFormSchema = z
@@ -20,17 +19,7 @@ export const ZAddTemplatePlacholderRecipientsFormSchema = z
     signingOrder: z.nativeEnum(DocumentSigningOrder),
     allowDictateNextSigner: z.boolean().default(false),
   })
-  .refine(
-    (schema) => {
-      const nonPlaceholderEmails = schema.signers
-        .map((signer) => signer.email.toLowerCase())
-        .filter((email) => !TEMPLATE_RECIPIENT_EMAIL_PLACEHOLDER_REGEX.test(email));
 
-      return new Set(nonPlaceholderEmails).size === nonPlaceholderEmails.length;
-    },
-    // Dirty hack to handle errors when .root is populated for an array type
-    { message: 'Signers must have unique emails', path: ['signers__root'] },
-  )
   .refine(
     /*
       Since placeholder emails are empty, we need to check that the names are unique.