feat: signing reminders (#1749)

packages/app-tests/e2e/envelope-editor-v2/envelope-settings.spec.ts

@@ -31,6 +31,12 @@ const TEST_SETTINGS_VALUES = {
   expirationMode: 'Custom duration',
   expirationAmount: 5,
   expirationUnit: 'Weeks',
+  reminderMode: 'Enabled',
+  reminderSendAfterAmount: 3,
+  reminderSendAfterUnit: 'Days',
+  reminderRepeatMode: 'Custom interval',
+  reminderRepeatAmount: 7,
+  reminderRepeatUnit: 'Days',
   accessAuth: 'Require account',
   actionAuth: 'Require password',
   visibility: 'Managers and above',
@@ -42,6 +48,10 @@ const DB_EXPECTED_VALUES = {
   timezone: 'Europe/London',
   distributionMethod: DocumentDistributionMethod.NONE,
   envelopeExpirationPeriod: { unit: 'week', amount: 5 },
+  reminderSettings: {
+    sendAfter: { unit: 'day', amount: 3 },
+    repeatEvery: { unit: 'day', amount: 7 },
+  },
   visibility: DocumentVisibility.MANAGER_AND_ABOVE,
   globalAccessAuth: ['ACCOUNT'],
   globalActionAuth: ['PASSWORD'],
@@ -130,6 +140,66 @@ const runSettingsFlow = async (
   await root.getByRole('option', { name: TEST_SETTINGS_VALUES.expirationUnit }).click();
   await clickSettingsDialogHeader(root);
 
+  // Configure reminder settings.
+  await root.getByRole('button', { name: 'Reminders' }).click();
+
+  await root.locator('[data-testid="reminder-mode-select"]').click();
+  await root.getByRole('option', { name: TEST_SETTINGS_VALUES.reminderMode }).click();
+  await clickSettingsDialogHeader(root);
+
+  await root.locator('[data-testid="reminder-send-after-amount"]').clear();
+  await root
+    .locator('[data-testid="reminder-send-after-amount"]')
+    .fill(String(TEST_SETTINGS_VALUES.reminderSendAfterAmount));
+
+  await root.locator('[data-testid="reminder-send-after-unit"]').click();
+  await root.getByRole('option', { name: TEST_SETTINGS_VALUES.reminderSendAfterUnit }).click();
+  await clickSettingsDialogHeader(root);
+
+  await root.locator('[data-testid="reminder-repeat-mode-select"]').click();
+  await root.getByRole('option', { name: TEST_SETTINGS_VALUES.reminderRepeatMode }).click();
+  await clickSettingsDialogHeader(root);
+
+  await root.locator('[data-testid="reminder-repeat-amount"]').clear();
+  await root
+    .locator('[data-testid="reminder-repeat-amount"]')
+    .fill(String(TEST_SETTINGS_VALUES.reminderRepeatAmount));
+
+  await root.locator('[data-testid="reminder-repeat-unit"]').click();
+  await root.getByRole('option', { name: TEST_SETTINGS_VALUES.reminderRepeatUnit }).click();
+  await clickSettingsDialogHeader(root);
+
+  const spinbuttons = root.getByRole('spinbutton');
+  await spinbuttons.first().clear();
+  await spinbuttons.first().fill(String(TEST_SETTINGS_VALUES.reminderSendAfterAmount));
+
+  const sendAfterUnitTrigger = root
+    .locator('button[role="combobox"]')
+    .filter({ hasText: /Days|Weeks|Months/ })
+    .first();
+  await sendAfterUnitTrigger.click();
+  await root.getByRole('option', { name: TEST_SETTINGS_VALUES.reminderSendAfterUnit }).click();
+  await clickSettingsDialogHeader(root);
+
+  const repeatModeSelect = root
+    .locator('button[role="combobox"]')
+    .filter({ hasText: /Custom interval|Don't repeat/ })
+    .first();
+  await repeatModeSelect.click();
+  await root.getByRole('option', { name: TEST_SETTINGS_VALUES.reminderRepeatMode }).click();
+  await clickSettingsDialogHeader(root);
+
+  await spinbuttons.last().clear();
+  await spinbuttons.last().fill(String(TEST_SETTINGS_VALUES.reminderRepeatAmount));
+
+  const repeatUnitTrigger = root
+    .locator('button[role="combobox"]')
+    .filter({ hasText: /Days|Weeks|Months/ })
+    .last();
+  await repeatUnitTrigger.click();
+  await root.getByRole('option', { name: TEST_SETTINGS_VALUES.reminderRepeatUnit }).click();
+  await clickSettingsDialogHeader(root);
+
   await root.getByRole('button', { name: 'Email' }).click();
   await root.locator('#recipientSigned').click();
   await root.locator('#recipientSigningRequest').click();
@@ -200,6 +270,27 @@ const runSettingsFlow = async (
       .first(),
   ).toBeVisible();
 
+  // Verify reminder settings persisted in UI.
+  await root.getByRole('button', { name: 'Reminders' }).click();
+  await expect(root.locator('[data-testid="reminder-mode-select"]')).toContainText(
+    TEST_SETTINGS_VALUES.reminderMode,
+  );
+  await expect(root.locator('[data-testid="reminder-send-after-amount"]')).toHaveValue(
+    String(TEST_SETTINGS_VALUES.reminderSendAfterAmount),
+  );
+  await expect(root.locator('[data-testid="reminder-send-after-unit"]')).toContainText(
+    TEST_SETTINGS_VALUES.reminderSendAfterUnit,
+  );
+  await expect(root.locator('[data-testid="reminder-repeat-mode-select"]')).toContainText(
+    TEST_SETTINGS_VALUES.reminderRepeatMode,
+  );
+  await expect(root.locator('[data-testid="reminder-repeat-amount"]')).toHaveValue(
+    String(TEST_SETTINGS_VALUES.reminderRepeatAmount),
+  );
+  await expect(root.locator('[data-testid="reminder-repeat-unit"]')).toContainText(
+    TEST_SETTINGS_VALUES.reminderRepeatUnit,
+  );
+
   await root.getByRole('button', { name: 'Email' }).click();
   await expect(root.locator('#recipientSigned')).toHaveAttribute('aria-checked', 'false');
   await expect(root.locator('#recipientSigningRequest')).toHaveAttribute('aria-checked', 'false');
@@ -285,6 +376,7 @@ const assertEnvelopeSettingsPersistedInDatabase = async ({
   expect(envelope.documentMeta.envelopeExpirationPeriod).toEqual(
     DB_EXPECTED_VALUES.envelopeExpirationPeriod,
   );
+  expect(envelope.documentMeta.reminderSettings).toEqual(DB_EXPECTED_VALUES.reminderSettings);
   expect(envelope.documentMeta.redirectUrl).toBe(TEST_SETTINGS_VALUES.redirectUrl);
   expect(envelope.documentMeta.emailReplyTo).toBe(TEST_SETTINGS_VALUES.replyTo);
   expect(envelope.documentMeta.subject).toBe(TEST_SETTINGS_VALUES.subject);

packages/app-tests/e2e/envelopes/envelope-expiration-settings.spec.ts

@@ -25,7 +25,7 @@ test('[ENVELOPE_EXPIRATION]: set custom expiration period at organisation level'
   await expect(page.getByRole('button', { name: 'Update' }).first()).toBeVisible();
 
   // Change the amount to 2.
-  const amountInput = page.getByRole('spinbutton');
+  const amountInput = page.getByTestId('envelope-expiration-amount');
   await amountInput.clear();
   await amountInput.fill('2');
 
@@ -33,9 +33,7 @@ test('[ENVELOPE_EXPIRATION]: set custom expiration period at organisation level'
   // In the duration mode, there's a mode select and a unit select.
   // The unit select is inside the duration row, after the number input.
   // Let's find the select trigger that contains the unit text.
-  const unitTrigger = page
-    .locator('button[role="combobox"]')
-    .filter({ hasText: /Months|Days|Weeks|Years/ });
+  const unitTrigger = page.getByTestId('envelope-expiration-unit');
 
   await unitTrigger.click();
   await page.getByRole('option', { name: 'Weeks' }).click();
@@ -65,9 +63,7 @@ test('[ENVELOPE_EXPIRATION]: disable expiration at organisation level', async ({
   await expect(page.getByRole('button', { name: 'Update' }).first()).toBeVisible();
 
   // Find the mode select (shows "Custom duration") and change to "Never expires".
-  const modeTrigger = page
-    .locator('button[role="combobox"]')
-    .filter({ hasText: 'Custom duration' });
+  const modeTrigger = page.getByTestId('envelope-expiration-mode');
   await modeTrigger.click();
   await page.getByRole('option', { name: 'Never expires' }).click();
 
@@ -118,11 +114,8 @@ test('[ENVELOPE_EXPIRATION]: team overrides organisation expiration', async ({ p
 
   await expect(page.getByRole('button', { name: 'Update' }).first()).toBeVisible();
 
-  // Scope to the "Default Envelope Expiration" form field section.
-  const expirationSection = page.getByText('Default Envelope Expiration').locator('..');
-
   // The expiration picker mode select should show "Inherit from organisation" by default.
-  const modeTrigger = expirationSection.locator('button[role="combobox"]').first();
+  const modeTrigger = page.getByTestId('envelope-expiration-mode');
   await expect(modeTrigger).toBeVisible();
 
   // Switch to custom duration.
@@ -130,13 +123,11 @@ test('[ENVELOPE_EXPIRATION]: team overrides organisation expiration', async ({ p
   await page.getByRole('option', { name: 'Custom duration' }).click();
 
   // Set to 5 days.
-  const amountInput = expirationSection.getByRole('spinbutton');
+  const amountInput = page.getByTestId('envelope-expiration-amount');
   await amountInput.clear();
   await amountInput.fill('5');
 
-  const unitTrigger = expirationSection
-    .locator('button[role="combobox"]')
-    .filter({ hasText: /Months|Days|Weeks|Years/ });
+  const unitTrigger = page.getByTestId('envelope-expiration-unit');
   await unitTrigger.click();
   await page.getByRole('option', { name: 'Days' }).click();
 

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

@@ -0,0 +1,77 @@
+import { useLingui } from '@lingui/react';
+import { Trans } from '@lingui/react/macro';
+import { RecipientRole } from '@prisma/client';
+import { match } from 'ts-pattern';
+
+import { RECIPIENT_ROLES_DESCRIPTION } from '@documenso/lib/constants/recipient-roles';
+
+import { Button, Section, Text } from '../components';
+import { TemplateDocumentImage } from './template-document-image';
+
+export interface TemplateDocumentReminderProps {
+  recipientName: string;
+  documentName: string;
+  signDocumentLink: string;
+  assetBaseUrl: string;
+  role: RecipientRole;
+}
+
+export const TemplateDocumentReminder = ({
+  recipientName,
+  documentName,
+  signDocumentLink,
+  assetBaseUrl,
+  role,
+}: TemplateDocumentReminderProps) => {
+  const { _ } = useLingui();
+
+  const { actionVerb } = RECIPIENT_ROLES_DESCRIPTION[role];
+
+  return (
+    <>
+      <TemplateDocumentImage className="mt-6" assetBaseUrl={assetBaseUrl} />
+
+      <Section>
+        <Text className="text-primary mx-auto mb-0 max-w-[80%] text-center text-lg font-semibold">
+          <Trans>
+            Reminder: Please {_(actionVerb).toLowerCase()} your document
+            <br />"{documentName}"
+          </Trans>
+        </Text>
+
+        <Text className="my-1 text-center text-base text-slate-400">
+          <Trans>Hi {recipientName},</Trans>
+        </Text>
+
+        <Text className="my-1 text-center text-base text-slate-400">
+          {match(role)
+            .with(RecipientRole.SIGNER, () => <Trans>Continue by signing the document.</Trans>)
+            .with(RecipientRole.VIEWER, () => <Trans>Continue by viewing the document.</Trans>)
+            .with(RecipientRole.APPROVER, () => <Trans>Continue by approving the document.</Trans>)
+            .with(RecipientRole.CC, () => '')
+            .with(RecipientRole.ASSISTANT, () => (
+              <Trans>Continue by assisting with the document.</Trans>
+            ))
+            .exhaustive()}
+        </Text>
+
+        <Section className="mb-6 mt-8 text-center">
+          <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"
+            href={signDocumentLink}
+          >
+            {match(role)
+              .with(RecipientRole.SIGNER, () => <Trans>Sign Document</Trans>)
+              .with(RecipientRole.VIEWER, () => <Trans>View Document</Trans>)
+              .with(RecipientRole.APPROVER, () => <Trans>Approve Document</Trans>)
+              .with(RecipientRole.CC, () => '')
+              .with(RecipientRole.ASSISTANT, () => <Trans>Assist Document</Trans>)
+              .exhaustive()}
+          </Button>
+        </Section>
+      </Section>
+    </>
+  );
+};
+
+export default TemplateDocumentReminder;

packages/email/templates/document-reminder.tsx

@@ -0,0 +1,91 @@
+import { msg } from '@lingui/core/macro';
+import { useLingui } from '@lingui/react';
+import { RecipientRole } from '@prisma/client';
+
+import { RECIPIENT_ROLES_DESCRIPTION } from '@documenso/lib/constants/recipient-roles';
+
+import { Body, Container, Head, Hr, Html, Img, Preview, Section, Text } from '../components';
+import { useBranding } from '../providers/branding';
+import { TemplateCustomMessageBody } from '../template-components/template-custom-message-body';
+import { TemplateDocumentReminder } from '../template-components/template-document-reminder';
+import { TemplateFooter } from '../template-components/template-footer';
+
+export type DocumentReminderEmailTemplateProps = {
+  recipientName: string;
+  documentName: string;
+  signDocumentLink: string;
+  assetBaseUrl?: string;
+  customBody?: string;
+  role: RecipientRole;
+};
+
+export const DocumentReminderEmailTemplate = ({
+  recipientName = 'John Doe',
+  documentName = 'Open Source Pledge.pdf',
+  signDocumentLink = 'https://documenso.com',
+  assetBaseUrl = 'http://localhost:3002',
+  customBody,
+  role = RecipientRole.SIGNER,
+}: DocumentReminderEmailTemplateProps) => {
+  const { _ } = useLingui();
+  const branding = useBranding();
+
+  const action = _(RECIPIENT_ROLES_DESCRIPTION[role].actionVerb).toLowerCase();
+
+  const previewText = msg`Reminder to ${action} ${documentName}`;
+
+  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"
+                />
+              )}
+
+              <TemplateDocumentReminder
+                recipientName={recipientName}
+                documentName={documentName}
+                signDocumentLink={signDocumentLink}
+                assetBaseUrl={assetBaseUrl}
+                role={role}
+              />
+            </Section>
+          </Container>
+
+          {customBody && (
+            <Container className="mx-auto mt-12 max-w-xl">
+              <Section>
+                <Text className="mt-2 text-base text-slate-400">
+                  <TemplateCustomMessageBody text={customBody} />
+                </Text>
+              </Section>
+            </Container>
+          )}
+
+          <Hr className="mx-auto mt-12 max-w-xl" />
+
+          <Container className="mx-auto max-w-xl">
+            <TemplateFooter />
+          </Container>
+        </Section>
+      </Body>
+    </Html>
+  );
+};
+
+export default DocumentReminderEmailTemplate;

packages/lib/client-only/hooks/use-editor-fields.ts

@@ -1,7 +1,7 @@
 import { useCallback, useEffect, useMemo, useState } from 'react';
 
 import { zodResolver } from '@hookform/resolvers/zod';
-import type { Field, Recipient } from '@prisma/client';
+import type { Field } from '@prisma/client';
 import { FieldType } from '@prisma/client';
 import { useFieldArray, useForm } from 'react-hook-form';
 import { z } from 'zod';
@@ -61,7 +61,7 @@ type UseEditorFieldsResponse = {
   getFieldsByRecipient: (recipientId: number) => TLocalField[];
 
   // Selected recipient
-  selectedRecipient: Recipient | null;
+  selectedRecipient: TEditorEnvelope['recipients'][number] | null;
   setSelectedRecipient: (recipientId: number | null) => void;
 
   resetForm: (fields?: Field[]) => void;

packages/lib/client-only/hooks/use-editor-recipients.ts

@@ -1,7 +1,7 @@
 import { useId } from 'react';
 
 import { zodResolver } from '@hookform/resolvers/zod';
-import { DocumentSigningOrder, type Recipient, RecipientRole } from '@prisma/client';
+import { DocumentSigningOrder, RecipientRole } from '@prisma/client';
 import type { UseFormReturn } from 'react-hook-form';
 import { useForm } from 'react-hook-form';
 import { prop, sortBy } from 'remeda';
@@ -39,7 +39,7 @@ type EditorRecipientsProps = {
 };
 
 type ResetFormOptions = {
-  recipients?: Recipient[];
+  recipients?: TEditorEnvelope['recipients'];
   documentMeta?: TEditorEnvelope['documentMeta'];
 };
 

packages/lib/client-only/recipient-type.ts

@@ -7,6 +7,8 @@ import {
   SigningStatus,
 } from '@prisma/client';
 
+type RecipientForType = Pick<Recipient, 'role' | 'signingStatus' | 'readStatus' | 'sendStatus'>;
+
 export enum RecipientStatusType {
   COMPLETED = 'completed',
   OPENED = 'opened',
@@ -16,7 +18,7 @@ export enum RecipientStatusType {
 }
 
 export const getRecipientType = (
-  recipient: Recipient,
+  recipient: RecipientForType,
   distributionMethod: DocumentDistributionMethod = DocumentDistributionMethod.EMAIL,
 ) => {
   if (recipient.role === RecipientRole.CC || recipient.signingStatus === SigningStatus.SIGNED) {
@@ -45,7 +47,7 @@ export const getRecipientType = (
   return RecipientStatusType.UNSIGNED;
 };
 
-export const getExtraRecipientsType = (extraRecipients: Recipient[]) => {
+export const getExtraRecipientsType = (extraRecipients: RecipientForType[]) => {
   const types = extraRecipients.map((r) => getRecipientType(r));
 
   if (types.includes(RecipientStatusType.UNSIGNED)) {

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

@@ -19,4 +19,7 @@ export const DOCUMENT_AUDIT_LOG_EMAIL_FORMAT = {
   [DOCUMENT_EMAIL_TYPE.DOCUMENT_COMPLETED]: {
     description: 'Document completed',
   },
+  [DOCUMENT_EMAIL_TYPE.REMINDER]: {
+    description: 'Signing Reminder',
+  },
 } satisfies Record<keyof typeof DOCUMENT_EMAIL_TYPE, unknown>;

packages/lib/constants/envelope-reminder.ts

@@ -0,0 +1,86 @@
+import type { DurationLikeObject } from 'luxon';
+import { Duration } from 'luxon';
+import { z } from 'zod';
+
+export const ZEnvelopeReminderDurationPeriod = z.object({
+  unit: z.enum(['day', 'week', 'month']),
+  amount: z.number().int().min(1),
+});
+
+export const ZEnvelopeReminderDisabledPeriod = z.object({
+  disabled: z.literal(true),
+});
+
+export const ZEnvelopeReminderPeriod = z.union([
+  ZEnvelopeReminderDurationPeriod,
+  ZEnvelopeReminderDisabledPeriod,
+]);
+
+export type TEnvelopeReminderPeriod = z.infer<typeof ZEnvelopeReminderPeriod>;
+export type TEnvelopeReminderDurationPeriod = z.infer<typeof ZEnvelopeReminderDurationPeriod>;
+
+export const ZEnvelopeReminderSettings = z.object({
+  sendAfter: ZEnvelopeReminderPeriod,
+  repeatEvery: ZEnvelopeReminderPeriod,
+});
+
+export type TEnvelopeReminderSettings = z.infer<typeof ZEnvelopeReminderSettings>;
+
+export const DEFAULT_ENVELOPE_REMINDER_SETTINGS: TEnvelopeReminderSettings = {
+  sendAfter: { unit: 'day', amount: 5 },
+  repeatEvery: { unit: 'day', amount: 2 },
+};
+
+const UNIT_TO_LUXON_KEY: Record<TEnvelopeReminderDurationPeriod['unit'], keyof DurationLikeObject> =
+  {
+    day: 'days',
+    week: 'weeks',
+    month: 'months',
+  };
+
+export const getEnvelopeReminderDuration = (period: TEnvelopeReminderDurationPeriod): Duration => {
+  return Duration.fromObject({ [UNIT_TO_LUXON_KEY[period.unit]]: period.amount });
+};
+
+/**
+ * Resolve the next reminder timestamp from the config and the last reminder sent time.
+ *
+ * - `null` config means reminders are disabled (inherit = no override, resolved as disabled).
+ * - `{ sendAfter: { disabled: true }, ... }` means never send the first reminder.
+ * - `{ repeatEvery: { disabled: true }, ... }` means don't repeat after the first reminder.
+ *
+ * `sentAt` is when the signing request was sent to this specific recipient.
+ *
+ * Returns the next Date the reminder should be sent, or null if no reminder should be sent.
+ */
+export const resolveNextReminderAt = (options: {
+  config: TEnvelopeReminderSettings | null;
+  sentAt: Date;
+  lastReminderSentAt: Date | null;
+}): Date | null => {
+  const { config, sentAt, lastReminderSentAt } = options;
+
+  if (!config) {
+    return null;
+  }
+
+  // If we haven't sent the first reminder yet, use sendAfter.
+  if (!lastReminderSentAt) {
+    if ('disabled' in config.sendAfter) {
+      return null;
+    }
+
+    const delay = getEnvelopeReminderDuration(config.sendAfter);
+
+    return new Date(sentAt.getTime() + delay.toMillis());
+  }
+
+  // For subsequent reminders, use repeatEvery.
+  if ('disabled' in config.repeatEvery) {
+    return null;
+  }
+
+  const interval = getEnvelopeReminderDuration(config.repeatEvery);
+
+  return new Date(lastReminderSentAt.getTime() + interval.toMillis());
+};

packages/lib/jobs/client.ts

@@ -16,8 +16,10 @@ import { CLEANUP_RATE_LIMITS_JOB_DEFINITION } from './definitions/internal/clean
 import { EXECUTE_WEBHOOK_JOB_DEFINITION } from './definitions/internal/execute-webhook';
 import { EXPIRE_RECIPIENTS_SWEEP_JOB_DEFINITION } from './definitions/internal/expire-recipients-sweep';
 import { PROCESS_RECIPIENT_EXPIRED_JOB_DEFINITION } from './definitions/internal/process-recipient-expired';
+import { PROCESS_SIGNING_REMINDER_JOB_DEFINITION } from './definitions/internal/process-signing-reminder';
 import { SEAL_DOCUMENT_JOB_DEFINITION } from './definitions/internal/seal-document';
 import { SEAL_DOCUMENT_SWEEP_JOB_DEFINITION } from './definitions/internal/seal-document-sweep';
+import { SEND_SIGNING_REMINDERS_SWEEP_JOB_DEFINITION } from './definitions/internal/send-signing-reminders-sweep';
 import { SYNC_EMAIL_DOMAINS_JOB_DEFINITION } from './definitions/internal/sync-email-domains';
 
 /**
@@ -43,6 +45,8 @@ export const jobsClient = new JobClient([
   EXECUTE_WEBHOOK_JOB_DEFINITION,
   EXPIRE_RECIPIENTS_SWEEP_JOB_DEFINITION,
   PROCESS_RECIPIENT_EXPIRED_JOB_DEFINITION,
+  SEND_SIGNING_REMINDERS_SWEEP_JOB_DEFINITION,
+  PROCESS_SIGNING_REMINDER_JOB_DEFINITION,
   CLEANUP_RATE_LIMITS_JOB_DEFINITION,
   SYNC_EMAIL_DOMAINS_JOB_DEFINITION,
 ] as const);

packages/lib/jobs/definitions/emails/send-signing-email.handler.ts

@@ -22,6 +22,7 @@ import {
   RECIPIENT_ROLE_TO_EMAIL_TYPE,
 } from '../../../constants/recipient-roles';
 import { getEmailContext } from '../../../server-only/email/get-email-context';
+import { updateRecipientNextReminder } from '../../../server-only/recipient/update-recipient-next-reminder';
 import { DOCUMENT_AUDIT_LOG_TYPE } from '../../../types/document-audit-logs';
 import { extractDerivedDocumentEmailSettings } from '../../../types/document-email';
 import { createDocumentAuditLogData } from '../../../utils/document-audit-logs';
@@ -206,6 +207,8 @@ export const run = async ({
     });
   }
 
+  const sentAt = new Date();
+
   await io.runTask('update-recipient', async () => {
     await prisma.recipient.update({
       where: {
@@ -213,26 +216,33 @@ export const run = async ({
       },
       data: {
         sendStatus: SendStatus.SENT,
+        sentAt,
       },
     });
   });
 
-  await io.runTask('store-audit-log', async () => {
-    await prisma.documentAuditLog.create({
-      data: createDocumentAuditLogData({
-        type: DOCUMENT_AUDIT_LOG_TYPE.EMAIL_SENT,
-        envelopeId: envelope.id,
-        user,
-        requestMetadata,
-        data: {
-          emailType: recipientEmailType,
-          recipientId: recipient.id,
-          recipientName: recipient.name,
-          recipientEmail: recipient.email,
-          recipientRole: recipient.role,
-          isResending: false,
-        },
-      }),
-    });
+  // Compute the first reminder time based on the envelope's effective settings.
+  await updateRecipientNextReminder({
+    recipientId: recipient.id,
+    envelopeId: envelope.id,
+    sentAt,
+    lastReminderSentAt: null,
+  });
+
+  await prisma.documentAuditLog.create({
+    data: createDocumentAuditLogData({
+      type: DOCUMENT_AUDIT_LOG_TYPE.EMAIL_SENT,
+      envelopeId: envelope.id,
+      user,
+      requestMetadata,
+      data: {
+        emailType: recipientEmailType,
+        recipientId: recipient.id,
+        recipientName: recipient.name,
+        recipientEmail: recipient.email,
+        recipientRole: recipient.role,
+        isResending: false,
+      },
+    }),
   });
 };

packages/lib/jobs/definitions/internal/process-signing-reminder.handler.ts

@@ -0,0 +1,222 @@
+import { createElement } from 'react';
+
+import { msg } from '@lingui/core/macro';
+import {
+  DocumentDistributionMethod,
+  DocumentStatus,
+  OrganisationType,
+  RecipientRole,
+  SendStatus,
+  SigningStatus,
+  WebhookTriggerEvents,
+} from '@prisma/client';
+
+import { mailer } from '@documenso/email/mailer';
+import DocumentReminderEmailTemplate from '@documenso/email/templates/document-reminder';
+import { prisma } from '@documenso/prisma';
+
+import { getI18nInstance } from '../../../client-only/providers/i18n-server';
+import { NEXT_PUBLIC_WEBAPP_URL } from '../../../constants/app';
+import { RECIPIENT_ROLES_DESCRIPTION } from '../../../constants/recipient-roles';
+import { getEmailContext } from '../../../server-only/email/get-email-context';
+import { updateRecipientNextReminder } from '../../../server-only/recipient/update-recipient-next-reminder';
+import { triggerWebhook } from '../../../server-only/webhooks/trigger/trigger-webhook';
+import { DOCUMENT_AUDIT_LOG_TYPE, DOCUMENT_EMAIL_TYPE } from '../../../types/document-audit-logs';
+import { extractDerivedDocumentEmailSettings } from '../../../types/document-email';
+import {
+  ZWebhookDocumentSchema,
+  mapEnvelopeToWebhookDocumentPayload,
+} from '../../../types/webhook-payload';
+import { createDocumentAuditLogData } from '../../../utils/document-audit-logs';
+import { renderCustomEmailTemplate } from '../../../utils/render-custom-email-template';
+import { renderEmailWithI18N } from '../../../utils/render-email-with-i18n';
+import type { JobRunIO } from '../../client/_internal/job';
+import type { TProcessSigningReminderJobDefinition } from './process-signing-reminder';
+
+export const run = async ({
+  payload,
+  io,
+}: {
+  payload: TProcessSigningReminderJobDefinition;
+  io: JobRunIO;
+}) => {
+  const { recipientId } = payload;
+  const now = new Date();
+
+  // Atomically claim this reminder by setting lastReminderSentAt and clearing
+  // nextReminderAt so no other sweep picks it up.
+  const updatedCount = await prisma.recipient.updateMany({
+    where: {
+      id: recipientId,
+      signingStatus: SigningStatus.NOT_SIGNED,
+      sendStatus: SendStatus.SENT,
+      role: { not: RecipientRole.CC },
+      envelope: {
+        status: DocumentStatus.PENDING,
+        deletedAt: null,
+      },
+    },
+    data: {
+      lastReminderSentAt: now,
+      nextReminderAt: null,
+    },
+  });
+
+  if (updatedCount.count === 0) {
+    io.logger.info(`Recipient ${recipientId} no longer eligible for reminder, skipping`);
+    return;
+  }
+
+  const recipient = await prisma.recipient.findFirst({
+    where: { id: recipientId },
+    include: {
+      envelope: {
+        include: {
+          documentMeta: true,
+          user: true,
+          recipients: true,
+          team: {
+            select: {
+              name: true,
+            },
+          },
+        },
+      },
+    },
+  });
+
+  if (!recipient) {
+    io.logger.warn(`Recipient ${recipientId} not found`);
+    return;
+  }
+
+  const { envelope } = recipient;
+
+  if (!envelope.documentMeta) {
+    io.logger.warn(`Envelope ${envelope.id} missing documentMeta`);
+    return;
+  }
+
+  // Skip if distribution method is NONE (manual link sharing, no emails).
+  if (envelope.documentMeta.distributionMethod === DocumentDistributionMethod.NONE) {
+    io.logger.info(`Envelope ${envelope.id} uses manual distribution, skipping email reminder`);
+    return;
+  }
+
+  if (!extractDerivedDocumentEmailSettings(envelope.documentMeta).recipientSigningRequest) {
+    io.logger.info(`Envelope ${envelope.id} has email signing requests disabled, skipping`);
+    return;
+  }
+
+  const { branding, emailLanguage, organisationType, senderEmail, replyToEmail } =
+    await getEmailContext({
+      emailType: 'RECIPIENT',
+      source: {
+        type: 'team',
+        teamId: envelope.teamId,
+      },
+      meta: envelope.documentMeta,
+    });
+
+  const i18n = await getI18nInstance(emailLanguage);
+
+  const recipientActionVerb = i18n
+    ._(RECIPIENT_ROLES_DESCRIPTION[recipient.role].actionVerb)
+    .toLowerCase();
+
+  let emailSubject = i18n._(
+    msg`Reminder: Please ${recipientActionVerb} the document "${envelope.title}"`,
+  );
+
+  if (organisationType === OrganisationType.ORGANISATION) {
+    emailSubject = i18n._(
+      msg`Reminder: ${envelope.team.name} invited you to ${recipientActionVerb} a document`,
+    );
+  }
+
+  const customEmailTemplate = {
+    'signer.name': recipient.name,
+    'signer.email': recipient.email,
+    'document.name': envelope.title,
+  };
+
+  if (envelope.documentMeta.subject) {
+    emailSubject = renderCustomEmailTemplate(
+      i18n._(msg`Reminder: ${envelope.documentMeta.subject}`),
+      customEmailTemplate,
+    );
+  }
+
+  const emailMessage = envelope.documentMeta.message
+    ? renderCustomEmailTemplate(envelope.documentMeta.message, customEmailTemplate)
+    : undefined;
+
+  const assetBaseUrl = NEXT_PUBLIC_WEBAPP_URL() || 'http://localhost:3000';
+  const signDocumentLink = `${NEXT_PUBLIC_WEBAPP_URL()}/sign/${recipient.token}`;
+
+  io.logger.info(
+    `Sending signing reminder for envelope ${envelope.id} to recipient ${recipient.id} (${recipient.email})`,
+  );
+
+  const template = createElement(DocumentReminderEmailTemplate, {
+    recipientName: recipient.name,
+    documentName: envelope.title,
+    assetBaseUrl,
+    signDocumentLink,
+    customBody: emailMessage,
+    role: recipient.role,
+  });
+
+  const [html, text] = await Promise.all([
+    renderEmailWithI18N(template, { lang: emailLanguage, branding }),
+    renderEmailWithI18N(template, {
+      lang: emailLanguage,
+      branding,
+      plainText: true,
+    }),
+  ]);
+
+  await mailer.sendMail({
+    to: {
+      name: recipient.name,
+      address: recipient.email,
+    },
+    from: senderEmail,
+    replyTo: replyToEmail,
+    subject: emailSubject,
+    html,
+    text,
+  });
+
+  await prisma.documentAuditLog.create({
+    data: createDocumentAuditLogData({
+      type: DOCUMENT_AUDIT_LOG_TYPE.EMAIL_SENT,
+      envelopeId: envelope.id,
+      data: {
+        recipientEmail: recipient.email,
+        recipientName: recipient.name,
+        recipientId: recipient.id,
+        recipientRole: recipient.role,
+        emailType: DOCUMENT_EMAIL_TYPE.REMINDER,
+        isResending: false,
+      },
+    }),
+  });
+
+  await triggerWebhook({
+    event: WebhookTriggerEvents.DOCUMENT_REMINDER_SENT,
+    data: ZWebhookDocumentSchema.parse(mapEnvelopeToWebhookDocumentPayload(envelope)),
+    userId: envelope.userId,
+    teamId: envelope.teamId,
+  });
+
+  // Compute the next reminder time (repeat interval).
+  if (recipient.sentAt) {
+    await updateRecipientNextReminder({
+      recipientId: recipient.id,
+      envelopeId: envelope.id,
+      sentAt: recipient.sentAt,
+      lastReminderSentAt: now,
+    });
+  }
+};

packages/lib/jobs/definitions/internal/process-signing-reminder.ts

@@ -0,0 +1,31 @@
+import { z } from 'zod';
+
+import { type JobDefinition } from '../../client/_internal/job';
+
+const PROCESS_SIGNING_REMINDER_JOB_DEFINITION_ID = 'internal.process-signing-reminder';
+
+const PROCESS_SIGNING_REMINDER_JOB_DEFINITION_SCHEMA = z.object({
+  recipientId: z.number(),
+});
+
+export type TProcessSigningReminderJobDefinition = z.infer<
+  typeof PROCESS_SIGNING_REMINDER_JOB_DEFINITION_SCHEMA
+>;
+
+export const PROCESS_SIGNING_REMINDER_JOB_DEFINITION = {
+  id: PROCESS_SIGNING_REMINDER_JOB_DEFINITION_ID,
+  name: 'Process Signing Reminder',
+  version: '1.0.0',
+  trigger: {
+    name: PROCESS_SIGNING_REMINDER_JOB_DEFINITION_ID,
+    schema: PROCESS_SIGNING_REMINDER_JOB_DEFINITION_SCHEMA,
+  },
+  handler: async ({ payload, io }) => {
+    const handler = await import('./process-signing-reminder.handler');
+
+    await handler.run({ payload, io });
+  },
+} as const satisfies JobDefinition<
+  typeof PROCESS_SIGNING_REMINDER_JOB_DEFINITION_ID,
+  TProcessSigningReminderJobDefinition
+>;

packages/lib/jobs/definitions/internal/send-signing-reminders-sweep.handler.ts

@@ -0,0 +1,49 @@
+import { DocumentStatus, RecipientRole, SendStatus, SigningStatus } from '@prisma/client';
+
+import { prisma } from '@documenso/prisma';
+
+import { jobs } from '../../client';
+import type { JobRunIO } from '../../client/_internal/job';
+import type { TSendSigningRemindersSweepJobDefinition } from './send-signing-reminders-sweep';
+
+export const run = async ({
+  io,
+}: {
+  payload: TSendSigningRemindersSweepJobDefinition;
+  io: JobRunIO;
+}) => {
+  const now = new Date();
+
+  const recipients = await prisma.recipient.findMany({
+    where: {
+      nextReminderAt: { lte: now },
+      signingStatus: SigningStatus.NOT_SIGNED,
+      sendStatus: SendStatus.SENT,
+      role: { not: RecipientRole.CC },
+      envelope: {
+        status: DocumentStatus.PENDING,
+        deletedAt: null,
+      },
+    },
+    select: { id: true },
+    take: 1000,
+  });
+
+  if (recipients.length === 0) {
+    io.logger.info('No recipients need signing reminders');
+    return;
+  }
+
+  io.logger.info(`Found ${recipients.length} recipients needing signing reminders`);
+
+  await Promise.allSettled(
+    recipients.map(async (recipient) => {
+      await jobs.triggerJob({
+        name: 'internal.process-signing-reminder',
+        payload: {
+          recipientId: recipient.id,
+        },
+      });
+    }),
+  );
+};

packages/lib/jobs/definitions/internal/send-signing-reminders-sweep.ts

@@ -0,0 +1,30 @@
+import { z } from 'zod';
+
+import { type JobDefinition } from '../../client/_internal/job';
+
+const SEND_SIGNING_REMINDERS_SWEEP_JOB_DEFINITION_ID = 'internal.send-signing-reminders-sweep';
+
+const SEND_SIGNING_REMINDERS_SWEEP_JOB_DEFINITION_SCHEMA = z.object({});
+
+export type TSendSigningRemindersSweepJobDefinition = z.infer<
+  typeof SEND_SIGNING_REMINDERS_SWEEP_JOB_DEFINITION_SCHEMA
+>;
+
+export const SEND_SIGNING_REMINDERS_SWEEP_JOB_DEFINITION = {
+  id: SEND_SIGNING_REMINDERS_SWEEP_JOB_DEFINITION_ID,
+  name: 'Send Signing Reminders Sweep',
+  version: '1.0.0',
+  trigger: {
+    name: SEND_SIGNING_REMINDERS_SWEEP_JOB_DEFINITION_ID,
+    schema: SEND_SIGNING_REMINDERS_SWEEP_JOB_DEFINITION_SCHEMA,
+    cron: '*/15 * * * *', // Every 15 minutes.
+  },
+  handler: async ({ payload, io }) => {
+    const handler = await import('./send-signing-reminders-sweep.handler');
+
+    await handler.run({ payload, io });
+  },
+} as const satisfies JobDefinition<
+  typeof SEND_SIGNING_REMINDERS_SWEEP_JOB_DEFINITION_ID,
+  TSendSigningRemindersSweepJobDefinition
+>;

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

@@ -442,6 +442,7 @@ export const completeDocumentWithToken = async ({
           where: { id: nextRecipient.id },
           data: {
             sendStatus: SendStatus.SENT,
+            sentAt: new Date(),
             ...(nextSigner && envelope.documentMeta?.allowDictateNextSigner
               ? {
                   name: nextSigner.name,

packages/lib/server-only/document/viewed-document.ts

@@ -69,6 +69,8 @@ export const viewedDocument = async ({
         // This handles cases where distribution is done manually
         sendStatus: SendStatus.SENT,
         readStatus: ReadStatus.OPENED,
+        // Only set sentAt if not already set (email may have been sent before they opened).
+        ...(!recipient.sentAt ? { sentAt: new Date() } : {}),
       },
     });
 
@@ -92,6 +94,9 @@ export const viewedDocument = async ({
     });
   });
 
+  // Don't schedule reminders for manually distributed documents —
+  // there's no email pathway to send them through.
+
   const envelope = await prisma.envelope.findUniqueOrThrow({
     where: {
       id: recipient.envelopeId,

packages/lib/server-only/envelope/update-envelope.ts

@@ -18,6 +18,7 @@ import {
 import { createDocumentAuthOptions, extractDocumentAuthMethods } from '../../utils/document-auth';
 import type { EnvelopeIdOptions } from '../../utils/envelope';
 import { buildTeamWhereQuery, canAccessTeamDocument } from '../../utils/teams';
+import { recomputeNextReminderForEnvelope } from '../recipient/update-recipient-next-reminder';
 import { triggerWebhook } from '../webhooks/trigger/trigger-webhook';
 import { getEnvelopeWhereInput } from './get-envelope-by-id';
 
@@ -354,6 +355,11 @@ export const updateEnvelope = async ({
     return result;
   });
 
+  // Recompute reminders for active recipients when reminder settings change.
+  if (meta && 'reminderSettings' in meta) {
+    await recomputeNextReminderForEnvelope(envelope.id);
+  }
+
   if (envelope.type === EnvelopeType.TEMPLATE) {
     await triggerWebhook({
       event: WebhookTriggerEvents.TEMPLATE_UPDATED,

packages/lib/server-only/recipient/update-recipient-next-reminder.ts

@@ -0,0 +1,112 @@
+import {
+  DocumentDistributionMethod,
+  RecipientRole,
+  SendStatus,
+  SigningStatus,
+} from '@prisma/client';
+
+import { prisma } from '@documenso/prisma';
+
+import {
+  ZEnvelopeReminderSettings,
+  resolveNextReminderAt,
+} from '../../constants/envelope-reminder';
+
+/**
+ * Compute and store `nextReminderAt` for a single recipient.
+ *
+ * Call this after:
+ * - Sending the signing email (sentAt is set)
+ * - Sending a reminder (lastReminderSentAt is updated)
+ *
+ * If `reminderSettings` is provided it's used directly, avoiding a query.
+ * Otherwise it's read from the envelope's documentMeta (already resolved
+ * from the org/team cascade at envelope creation time).
+ */
+export const updateRecipientNextReminder = async (options: {
+  recipientId: number;
+  envelopeId: string;
+  sentAt: Date;
+  lastReminderSentAt: Date | null;
+  reminderSettings?: ReturnType<typeof ZEnvelopeReminderSettings.parse> | null;
+}) => {
+  const { recipientId, envelopeId, sentAt, lastReminderSentAt } = options;
+
+  let settings = options.reminderSettings;
+
+  if (settings === undefined) {
+    const envelope = await prisma.envelope.findFirst({
+      where: { id: envelopeId },
+      select: { documentMeta: { select: { reminderSettings: true } } },
+    });
+
+    settings = envelope?.documentMeta?.reminderSettings
+      ? ZEnvelopeReminderSettings.parse(envelope.documentMeta.reminderSettings)
+      : null;
+  }
+
+  const nextReminderAt = resolveNextReminderAt({
+    config: settings,
+    sentAt,
+    lastReminderSentAt,
+  });
+
+  await prisma.recipient.update({
+    where: { id: recipientId },
+    data: { nextReminderAt },
+  });
+};
+
+/**
+ * Recompute `nextReminderAt` for all active (unsigned, sent) recipients
+ * of a given envelope. Call when document-level reminder settings change.
+ */
+export const recomputeNextReminderForEnvelope = async (envelopeId: string) => {
+  const envelope = await prisma.envelope.findFirst({
+    where: { id: envelopeId },
+    select: {
+      documentMeta: {
+        select: { reminderSettings: true, distributionMethod: true },
+      },
+    },
+  });
+
+  // No reminders for manually distributed documents.
+  const isEmailDistribution =
+    envelope?.documentMeta?.distributionMethod !== DocumentDistributionMethod.NONE;
+
+  const settings =
+    isEmailDistribution && envelope?.documentMeta?.reminderSettings
+      ? ZEnvelopeReminderSettings.parse(envelope.documentMeta.reminderSettings)
+      : null;
+
+  const recipients = await prisma.recipient.findMany({
+    where: {
+      envelopeId,
+      signingStatus: SigningStatus.NOT_SIGNED,
+      sendStatus: SendStatus.SENT,
+      sentAt: { not: null },
+      role: { not: RecipientRole.CC },
+    },
+    select: { id: true, sentAt: true, lastReminderSentAt: true },
+  });
+
+  await Promise.all(
+    recipients.map(async (recipient) => {
+      if (!recipient.sentAt) {
+        return;
+      }
+
+      const nextReminderAt = resolveNextReminderAt({
+        config: settings,
+        sentAt: recipient.sentAt,
+        lastReminderSentAt: recipient.lastReminderSentAt,
+      });
+
+      await prisma.recipient.update({
+        where: { id: recipient.id },
+        data: { nextReminderAt },
+      });
+    }),
+  );
+};

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

@@ -705,6 +705,7 @@ export const createDocumentFromDirectTemplate = async ({
           where: { id: nextRecipient.id },
           data: {
             sendStatus: SendStatus.SENT,
+            sentAt: new Date(),
             ...(nextSigner && documentMeta?.allowDictateNextSigner
               ? {
                   name: nextSigner.name,

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

@@ -63,6 +63,7 @@ export const ZDocumentAuditLogEmailTypeSchema = z.enum([
   'ASSISTING_REQUEST',
   'CC',
   'DOCUMENT_COMPLETED',
+  'REMINDER',
 ]);
 
 export const ZDocumentMetaDiffTypeSchema = z.enum([

packages/lib/types/document-meta.ts

@@ -4,6 +4,7 @@ import { z } from 'zod';
 
 import { VALID_DATE_FORMAT_VALUES } from '@documenso/lib/constants/date-formats';
 import { ZEnvelopeExpirationPeriod } from '@documenso/lib/constants/envelope-expiration';
+import { ZEnvelopeReminderSettings } from '@documenso/lib/constants/envelope-reminder';
 import { SUPPORTED_LANGUAGE_CODES } from '@documenso/lib/constants/i18n';
 import { isValidRedirectUrl } from '@documenso/lib/utils/is-valid-redirect-url';
 import { zEmail } from '@documenso/lib/utils/zod';
@@ -131,6 +132,7 @@ export const ZDocumentMetaCreateSchema = z.object({
   emailReplyTo: zEmail().nullish(),
   emailSettings: ZDocumentEmailSettingsSchema.nullish(),
   envelopeExpirationPeriod: ZEnvelopeExpirationPeriod.nullish(),
+  reminderSettings: ZEnvelopeReminderSettings.nullish(),
 });
 
 export type TDocumentMetaCreate = z.infer<typeof ZDocumentMetaCreateSchema>;

packages/lib/types/document.ts

@@ -72,6 +72,7 @@ export const ZDocumentSchema = LegacyDocumentSchema.pick({
     emailId: true,
     emailReplyTo: true,
     envelopeExpirationPeriod: true,
+    reminderSettings: true,
   }).extend({
     password: z.string().nullable().default(null),
     documentId: z.number().default(-1).optional(),

packages/lib/types/envelope-editor.ts

@@ -43,6 +43,7 @@ export const ZEnvelopeEditorSettingsSchema = z.object({
       allowConfigureRedirectUrl: z.boolean(),
       allowConfigureDistribution: z.boolean(),
       allowConfigureExpirationPeriod: z.boolean(),
+      allowConfigureReminders: z.boolean(),
       allowConfigureEmailSender: z.boolean(),
       allowConfigureEmailReplyTo: z.boolean(),
     })
@@ -122,6 +123,7 @@ export const DEFAULT_EDITOR_CONFIG: EnvelopeEditorConfig = {
     allowConfigureRedirectUrl: true,
     allowConfigureDistribution: true,
     allowConfigureExpirationPeriod: true,
+    allowConfigureReminders: true,
     allowConfigureEmailSender: true,
     allowConfigureEmailReplyTo: true,
   },
@@ -180,6 +182,7 @@ export const DEFAULT_EMBEDDED_EDITOR_CONFIG = {
     allowConfigureRedirectUrl: true,
     allowConfigureDistribution: true,
     allowConfigureExpirationPeriod: true,
+    allowConfigureReminders: true,
     allowConfigureEmailSender: true,
     allowConfigureEmailReplyTo: true,
   },
@@ -271,6 +274,7 @@ export const ZEditorEnvelopeSchema = EnvelopeSchema.pick({
     emailId: true,
     emailReplyTo: true,
     envelopeExpirationPeriod: true,
+    reminderSettings: true,
   }),
   recipients: ZEnvelopeRecipientLiteSchema.array(),
   fields: ZEnvelopeFieldSchema.array(),

packages/lib/types/recipient.ts

@@ -118,6 +118,13 @@ export const ZEnvelopeRecipientManySchema = ZRecipientManySchema.omit({
   templateId: true,
 });
 
+export type TRecipientSchema = z.infer<typeof ZRecipientSchema>;
+export type TRecipientLite = z.infer<typeof ZRecipientLiteSchema>;
+export type TRecipientMany = z.infer<typeof ZRecipientManySchema>;
+export type TEnvelopeRecipientSchema = z.infer<typeof ZEnvelopeRecipientSchema>;
+export type TEnvelopeRecipientLite = z.infer<typeof ZEnvelopeRecipientLiteSchema>;
+export type TEnvelopeRecipientMany = z.infer<typeof ZEnvelopeRecipientManySchema>;
+
 export const ZRecipientEmailSchema = z.union([
   z.literal(''),
   zEmail('Invalid email').trim().toLowerCase().max(254),

packages/lib/utils/document.ts

@@ -66,6 +66,9 @@ export const extractDerivedDocumentMeta = (
     // Envelope expiration.
     envelopeExpirationPeriod:
       meta.envelopeExpirationPeriod ?? settings.envelopeExpirationPeriod ?? null,
+
+    // Reminder settings.
+    reminderSettings: meta.reminderSettings ?? settings.reminderSettings ?? null,
   } satisfies Omit<DocumentMeta, 'id'>;
 };
 

packages/lib/utils/embed-config.ts

@@ -67,6 +67,9 @@ export const buildEmbeddedFeatures = (
             allowConfigureExpirationPeriod:
               features.settings?.allowConfigureExpirationPeriod ??
               DEFAULT_EMBEDDED_EDITOR_CONFIG.settings.allowConfigureExpirationPeriod,
+            allowConfigureReminders:
+              features.settings?.allowConfigureReminders ??
+              DEFAULT_EMBEDDED_EDITOR_CONFIG.settings.allowConfigureReminders,
             allowConfigureEmailSender:
               features.settings?.allowConfigureEmailSender ??
               DEFAULT_EMBEDDED_EDITOR_CONFIG.settings.allowConfigureEmailSender,

packages/lib/utils/envelope.ts

@@ -252,7 +252,7 @@ export type EnvelopeItemPermissions = {
 
 export const getEnvelopeItemPermissions = (
   envelope: Pick<Envelope, 'completedAt' | 'deletedAt' | 'type' | 'status'>,
-  recipients: Recipient[],
+  recipients: Pick<Recipient, 'role' | 'signingStatus' | 'sendStatus'>[],
 ): EnvelopeItemPermissions => {
   // Always reject completed/rejected/deleted envelopes.
   if (

packages/lib/utils/organisations.ts

@@ -9,6 +9,7 @@ import type { ORGANISATION_MEMBER_ROLE_MAP } from '@documenso/lib/constants/orga
 
 import { DEFAULT_DOCUMENT_DATE_FORMAT } from '../constants/date-formats';
 import { DEFAULT_ENVELOPE_EXPIRATION_PERIOD } from '../constants/envelope-expiration';
+import { DEFAULT_ENVELOPE_REMINDER_SETTINGS } from '../constants/envelope-reminder';
 import {
   LOWEST_ORGANISATION_ROLE,
   ORGANISATION_MEMBER_ROLE_HIERARCHY,
@@ -142,6 +143,8 @@ export const generateDefaultOrganisationSettings = (): Omit<
 
     envelopeExpirationPeriod: DEFAULT_ENVELOPE_EXPIRATION_PERIOD,
 
+    reminderSettings: DEFAULT_ENVELOPE_REMINDER_SETTINGS,
+
     aiFeaturesEnabled: false,
   };
 };

packages/lib/utils/recipients.ts

@@ -1,10 +1,11 @@
 import type { Envelope } from '@prisma/client';
-import { type Field, type Recipient, RecipientRole, SigningStatus } from '@prisma/client';
+import { type Field, RecipientRole, SigningStatus } from '@prisma/client';
 
 import { isSignatureFieldType } from '@documenso/prisma/guards/is-signature-field';
 
 import { NEXT_PUBLIC_WEBAPP_URL } from '../constants/app';
 import { AppError, AppErrorCode } from '../errors/app-error';
+import type { TRecipientLite } from '../types/recipient';
 import { extractLegacyIds } from '../universal/id';
 import { zEmail } from './zod';
 
@@ -20,7 +21,7 @@ export const RECIPIENT_ROLES_THAT_REQUIRE_FIELDS = [RecipientRole.SIGNER] as con
  *
  * Currently only SIGNERs are validated - they must have at least one signature field.
  */
-export const getRecipientsWithMissingFields = <T extends Pick<Recipient, 'id' | 'role'>>(
+export const getRecipientsWithMissingFields = <T extends Pick<TRecipientLite, 'id' | 'role'>>(
   recipients: T[],
   fields: Pick<Field, 'type' | 'recipientId'>[],
 ): T[] => {
@@ -42,7 +43,10 @@ export const formatSigningLink = (token: string) => `${NEXT_PUBLIC_WEBAPP_URL()}
 /**
  * Whether a recipient can be modified by the document owner.
  */
-export const canRecipientBeModified = (recipient: Recipient, fields: Field[]) => {
+export const canRecipientBeModified = (
+  recipient: TRecipientLite,
+  fields: Pick<Field, 'recipientId' | 'inserted'>[],
+) => {
   if (!recipient) {
     return false;
   }
@@ -72,7 +76,10 @@ export const canRecipientBeModified = (recipient: Recipient, fields: Field[]) =>
  * - They are not a Viewer or CCer
  * - They can be modified (canRecipientBeModified)
  */
-export const canRecipientFieldsBeModified = (recipient: Recipient, fields: Field[]) => {
+export const canRecipientFieldsBeModified = (
+  recipient: TRecipientLite,
+  fields: Pick<Field, 'recipientId' | 'inserted'>[],
+) => {
   if (!canRecipientBeModified(recipient, fields)) {
     return false;
   }
@@ -81,7 +88,7 @@ export const canRecipientFieldsBeModified = (recipient: Recipient, fields: Field
 };
 
 export const mapRecipientToLegacyRecipient = (
-  recipient: Recipient,
+  recipient: TRecipientLite,
   envelope: Pick<Envelope, 'type' | 'secondaryId'>,
 ) => {
   const legacyId = extractLegacyIds(envelope);
@@ -92,6 +99,7 @@ export const mapRecipientToLegacyRecipient = (
   };
 };
 
+
 export const findRecipientByEmail = <T extends { email: string }>({
   recipients,
   userEmail,
@@ -102,7 +110,7 @@ export const findRecipientByEmail = <T extends { email: string }>({
   teamEmail?: string | null;
 }) => recipients.find((r) => r.email === userEmail || (teamEmail && r.email === teamEmail));
 
-export const isRecipientEmailValidForSending = (recipient: Pick<Recipient, 'email'>) => {
+export const isRecipientEmailValidForSending = (recipient: Pick<TRecipientLite, 'email'>) => {
   return zEmail().safeParse(recipient.email).success;
 };
 

packages/lib/utils/teams.ts

@@ -208,6 +208,8 @@ export const generateDefaultTeamSettings = (): Omit<TeamGlobalSettings, 'id' | '
 
     envelopeExpirationPeriod: null,
 
+    reminderSettings: null,
+
     aiFeaturesEnabled: null,
   };
 };

packages/prisma/migrations/20260401000000_add_reminder_settings/migration.sql

@@ -0,0 +1,16 @@
+-- AlterTable
+ALTER TABLE "DocumentMeta" ADD COLUMN     "reminderSettings" JSONB;
+
+-- AlterTable
+ALTER TABLE "OrganisationGlobalSettings" ADD COLUMN     "reminderSettings" JSONB;
+
+-- AlterTable
+ALTER TABLE "TeamGlobalSettings" ADD COLUMN     "reminderSettings" JSONB;
+
+-- AlterTable
+ALTER TABLE "Recipient" ADD COLUMN     "sentAt" TIMESTAMP(3),
+ADD COLUMN     "lastReminderSentAt" TIMESTAMP(3),
+ADD COLUMN     "nextReminderAt" TIMESTAMP(3);
+
+-- CreateIndex
+CREATE INDEX "Recipient_nextReminderAt_idx" ON "Recipient"("nextReminderAt");

packages/prisma/schema.prisma

@@ -507,7 +507,7 @@ enum DocumentDistributionMethod {
   NONE
 }
 
-/// @zod.import(["import { ZDocumentEmailSettingsSchema } from '@documenso/lib/types/document-email';", "import { ZEnvelopeExpirationPeriod as ZEnvelopeExpirationPeriodSchema } from '@documenso/lib/constants/envelope-expiration';"])
+/// @zod.import(["import { ZDocumentEmailSettingsSchema } from '@documenso/lib/types/document-email';", "import { ZEnvelopeExpirationPeriod as ZEnvelopeExpirationPeriodSchema } from '@documenso/lib/constants/envelope-expiration';", "import { ZEnvelopeReminderSettings as ZEnvelopeReminderSettingsSchema } from '@documenso/lib/constants/envelope-reminder';"])
 model DocumentMeta {
   id                     String               @id @default(cuid())
   subject                String?
@@ -531,6 +531,8 @@ model DocumentMeta {
 
   envelopeExpirationPeriod Json? /// [EnvelopeExpirationPeriod] @zod.custom.use(ZEnvelopeExpirationPeriodSchema)
 
+  reminderSettings Json? /// [EnvelopeReminderSettings] @zod.custom.use(ZEnvelopeReminderSettingsSchema)
+
   envelope Envelope?
 }
 
@@ -587,7 +589,10 @@ model Recipient {
   expired              DateTime? // deprecated Not in use. To be removed in a future migration.
   expiresAt            DateTime?
   expirationNotifiedAt DateTime?
+  sentAt               DateTime?
   signedAt             DateTime?
+  lastReminderSentAt   DateTime?
+  nextReminderAt       DateTime?
   authOptions          Json? /// [RecipientAuthOptions] @zod.custom.use(ZRecipientAuthOptionsSchema)
   signingOrder         Int? /// @zod.number.describe("The order in which the recipient should sign the document. Only works if the document is set to sequential signing.")
   rejectionReason      String?
@@ -607,6 +612,7 @@ model Recipient {
   @@index([email, documentDeletedAt, envelopeId], map: "Recipient_email_documentDeletedAt_envelopeId_idx")
   @@index([email, envelopeId], map: "Recipient_email_envelopeId_idx")
   @@index([email, signingStatus, envelopeId, role], map: "Recipient_email_signingStatus_envelopeId_role_idx")
+  @@index([nextReminderAt])
   @@index([email(ops: raw("gin_trgm_ops"))], map: "Recipient_email_trgm_idx", type: Gin)
   @@index([name(ops: raw("gin_trgm_ops"))], map: "Recipient_name_trgm_idx", type: Gin)
 }
@@ -825,7 +831,7 @@ enum OrganisationMemberInviteStatus {
   DECLINED
 }
 
-/// @zod.import(["import { ZDocumentEmailSettingsSchema } from '@documenso/lib/types/document-email';", "import { ZDefaultRecipientsSchema } from '@documenso/lib/types/default-recipients';", "import { ZEnvelopeExpirationPeriod as ZEnvelopeExpirationPeriodSchema } from '@documenso/lib/constants/envelope-expiration';"])
+/// @zod.import(["import { ZDocumentEmailSettingsSchema } from '@documenso/lib/types/document-email';", "import { ZDefaultRecipientsSchema } from '@documenso/lib/types/default-recipients';", "import { ZEnvelopeExpirationPeriod as ZEnvelopeExpirationPeriodSchema } from '@documenso/lib/constants/envelope-expiration';", "import { ZEnvelopeReminderSettings as ZEnvelopeReminderSettingsSchema } from '@documenso/lib/constants/envelope-reminder';"])
 model OrganisationGlobalSettings {
   id           String        @id
   organisation Organisation?
@@ -859,11 +865,13 @@ model OrganisationGlobalSettings {
 
   envelopeExpirationPeriod Json? /// [EnvelopeExpirationPeriod] @zod.custom.use(ZEnvelopeExpirationPeriodSchema)
 
+  reminderSettings Json? /// [EnvelopeReminderSettings] @zod.custom.use(ZEnvelopeReminderSettingsSchema)
+
   // AI features settings.
   aiFeaturesEnabled Boolean @default(false)
 }
 
-/// @zod.import(["import { ZDocumentEmailSettingsSchema } from '@documenso/lib/types/document-email';", "import { ZDefaultRecipientsSchema } from '@documenso/lib/types/default-recipients';", "import { ZEnvelopeExpirationPeriod as ZEnvelopeExpirationPeriodSchema } from '@documenso/lib/constants/envelope-expiration';"])
+/// @zod.import(["import { ZDocumentEmailSettingsSchema } from '@documenso/lib/types/document-email';", "import { ZDefaultRecipientsSchema } from '@documenso/lib/types/default-recipients';", "import { ZEnvelopeExpirationPeriod as ZEnvelopeExpirationPeriodSchema } from '@documenso/lib/constants/envelope-expiration';", "import { ZEnvelopeReminderSettings as ZEnvelopeReminderSettingsSchema } from '@documenso/lib/constants/envelope-reminder';"])
 model TeamGlobalSettings {
   id   String @id
   team Team?
@@ -898,6 +906,8 @@ model TeamGlobalSettings {
 
   envelopeExpirationPeriod Json? /// [EnvelopeExpirationPeriod] @zod.custom.use(ZEnvelopeExpirationPeriodSchema)
 
+  reminderSettings Json? /// [EnvelopeReminderSettings] @zod.custom.use(ZEnvelopeReminderSettingsSchema)
+
   // AI features settings.
   aiFeaturesEnabled Boolean?
 }

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

@@ -5,14 +5,14 @@ import { authenticatedProcedure } from '../trpc';
 import {
   ZUpdateDocumentRequestSchema,
   ZUpdateDocumentResponseSchema,
+  updateDocumentMeta,
 } from './update-document.types';
-import { updateDocumentMeta as updateDocumentTrpcMeta } from './update-document.types';
 
 /**
  * Public route.
  */
 export const updateDocumentRoute = authenticatedProcedure
-  .meta(updateDocumentTrpcMeta)
+  .meta(updateDocumentMeta)
   .input(ZUpdateDocumentRequestSchema)
   .output(ZUpdateDocumentResponseSchema)
   .mutation(async ({ input, ctx }) => {

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

@@ -39,6 +39,7 @@ export const updateOrganisationSettingsRoute = authenticatedProcedure
       defaultRecipients,
       delegateDocumentOwnership,
       envelopeExpirationPeriod,
+      reminderSettings,
 
       // Branding related settings.
       brandingEnabled,
@@ -151,6 +152,7 @@ export const updateOrganisationSettingsRoute = authenticatedProcedure
             delegateDocumentOwnership: derivedDelegateDocumentOwnership,
             envelopeExpirationPeriod:
               envelopeExpirationPeriod === null ? Prisma.DbNull : envelopeExpirationPeriod,
+            reminderSettings: reminderSettings === null ? Prisma.DbNull : reminderSettings,
 
             // Branding related settings.
             brandingEnabled,

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

@@ -1,6 +1,7 @@
 import { z } from 'zod';
 
 import { ZEnvelopeExpirationPeriod } from '@documenso/lib/constants/envelope-expiration';
+import { ZEnvelopeReminderSettings } from '@documenso/lib/constants/envelope-reminder';
 import { SUPPORTED_LANGUAGE_CODES } from '@documenso/lib/constants/i18n';
 import { ZDefaultRecipientsSchema } from '@documenso/lib/types/default-recipients';
 import { ZDocumentEmailSettingsSchema } from '@documenso/lib/types/document-email';
@@ -28,6 +29,7 @@ export const ZUpdateOrganisationSettingsRequestSchema = z.object({
     defaultRecipients: ZDefaultRecipientsSchema.nullish(),
     delegateDocumentOwnership: z.boolean().nullish(),
     envelopeExpirationPeriod: ZEnvelopeExpirationPeriod.optional(),
+    reminderSettings: ZEnvelopeReminderSettings.optional(),
 
     // Branding related settings.
     brandingEnabled: z.boolean().optional(),

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

@@ -41,6 +41,7 @@ export const updateTeamSettingsRoute = authenticatedProcedure
       drawSignatureEnabled,
       delegateDocumentOwnership,
       envelopeExpirationPeriod,
+      reminderSettings,
 
       // Branding related settings.
       brandingEnabled,
@@ -157,6 +158,7 @@ export const updateTeamSettingsRoute = authenticatedProcedure
             delegateDocumentOwnership,
             envelopeExpirationPeriod:
               envelopeExpirationPeriod === null ? Prisma.DbNull : envelopeExpirationPeriod,
+            reminderSettings: reminderSettings === null ? Prisma.DbNull : reminderSettings,
 
             // Branding related settings.
             brandingEnabled,

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

@@ -1,6 +1,7 @@
 import { z } from 'zod';
 
 import { ZEnvelopeExpirationPeriod } from '@documenso/lib/constants/envelope-expiration';
+import { ZEnvelopeReminderSettings } from '@documenso/lib/constants/envelope-reminder';
 import { SUPPORTED_LANGUAGE_CODES } from '@documenso/lib/constants/i18n';
 import { ZDefaultRecipientsSchema } from '@documenso/lib/types/default-recipients';
 import { ZDocumentEmailSettingsSchema } from '@documenso/lib/types/document-email';
@@ -31,6 +32,7 @@ export const ZUpdateTeamSettingsRequestSchema = z.object({
     drawSignatureEnabled: z.boolean().nullish(),
     delegateDocumentOwnership: z.boolean().nullish(),
     envelopeExpirationPeriod: ZEnvelopeExpirationPeriod.nullish(),
+    reminderSettings: ZEnvelopeReminderSettings.nullish(),
 
     // Branding related settings.
     brandingEnabled: z.boolean().nullish(),

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

@@ -2,12 +2,13 @@ import { useState } from 'react';
 
 import { useLingui } from '@lingui/react';
 import { Trans } from '@lingui/react/macro';
-import type { DocumentMeta, Field, Recipient } from '@prisma/client';
+import type { DocumentMeta, Field } from '@prisma/client';
 import { SigningStatus } from '@prisma/client';
 import { Clock, EyeOffIcon } from 'lucide-react';
 
 import { PDF_VIEWER_PAGE_SELECTOR } from '@documenso/lib/constants/pdf-viewer';
 import { isTemplateRecipientEmailPlaceholder } from '@documenso/lib/constants/template';
+import type { TRecipientLite } from '@documenso/lib/types/recipient';
 import { parseMessageDescriptor } from '@documenso/lib/utils/i18n';
 import { extractInitials } from '@documenso/lib/utils/recipient-formatter';
 import { FieldRootContainer } from '@documenso/ui/components/field/field';
@@ -34,7 +35,7 @@ const getRecipientDisplayText = (recipient: { name: string; email: string }) =>
 };
 
 export type DocumentField = Field & {
-  recipient: Pick<Recipient, 'name' | 'email' | 'signingStatus'>;
+  recipient: Pick<TRecipientLite, 'name' | 'email' | 'signingStatus'>;
 };
 
 export type DocumentReadOnlyFieldsProps = {
@@ -68,7 +69,7 @@ export type DocumentReadOnlyFieldsProps = {
 
 export const mapFieldsWithRecipients = (
   fields: Field[],
-  recipients: Recipient[],
+  recipients: TRecipientLite[],
 ): DocumentField[] => {
   return fields.map((field) => {
     const recipient = recipients.find((recipient) => recipient.id === field.recipientId) || {

packages/ui/components/document/expiration-period-picker.tsx

@@ -90,7 +90,7 @@ export const ExpirationPeriodPicker = ({
   return (
     <div className="flex flex-col gap-2">
       <Select value={mode} onValueChange={onModeChange} disabled={disabled}>
-        <SelectTrigger className="bg-background">
+        <SelectTrigger className="bg-background" data-testid="envelope-expiration-mode">
           <SelectValue />
         </SelectTrigger>
 
@@ -113,13 +113,14 @@ export const ExpirationPeriodPicker = ({
             type="number"
             min={1}
             className="w-20 bg-background"
+            data-testid="envelope-expiration-amount"
             value={amount}
             onChange={(e) => onAmountChange(Number(e.target.value))}
             disabled={disabled}
           />
 
           <Select value={unit} onValueChange={onUnitChange} disabled={disabled}>
-            <SelectTrigger className="flex-1 bg-background">
+            <SelectTrigger className="flex-1 bg-background" data-testid="envelope-expiration-unit">
               <SelectValue />
             </SelectTrigger>
 

packages/ui/components/document/reminder-settings-picker.tsx

@@ -0,0 +1,266 @@
+import { Plural, Trans } from '@lingui/react/macro';
+
+import type {
+  TEnvelopeReminderDurationPeriod,
+  TEnvelopeReminderPeriod,
+  TEnvelopeReminderSettings,
+} from '@documenso/lib/constants/envelope-reminder';
+import { Input } from '@documenso/ui/primitives/input';
+import { Label } from '@documenso/ui/primitives/label';
+import {
+  Select,
+  SelectContent,
+  SelectItem,
+  SelectTrigger,
+  SelectValue,
+} from '@documenso/ui/primitives/select';
+
+type ReminderMode = 'enabled' | 'disabled' | 'inherit';
+
+const getMode = (value: TEnvelopeReminderSettings | null | undefined): ReminderMode => {
+  if (value === null || value === undefined) {
+    return 'inherit';
+  }
+
+  if ('disabled' in value.sendAfter) {
+    return 'disabled';
+  }
+
+  return 'enabled';
+};
+
+const getPeriodAmount = (period: TEnvelopeReminderPeriod | undefined): number => {
+  if (period && 'amount' in period) {
+    return period.amount;
+  }
+
+  return 1;
+};
+
+const getPeriodUnit = (
+  period: TEnvelopeReminderPeriod | undefined,
+): TEnvelopeReminderDurationPeriod['unit'] => {
+  if (period && 'unit' in period) {
+    return period.unit;
+  }
+
+  return 'day';
+};
+
+export type ReminderSettingsPickerProps = {
+  value: TEnvelopeReminderSettings | null | undefined;
+  onChange: (value: TEnvelopeReminderSettings | null) => void;
+  disabled?: boolean;
+  inheritLabel?: string;
+};
+
+export const ReminderSettingsPicker = ({
+  value,
+  onChange,
+  disabled = false,
+  inheritLabel,
+}: ReminderSettingsPickerProps) => {
+  const mode = getMode(value);
+
+  const sendAfterAmount = getPeriodAmount(value?.sendAfter);
+  const sendAfterUnit = getPeriodUnit(value?.sendAfter);
+  const repeatEveryAmount = getPeriodAmount(value?.repeatEvery);
+  const repeatEveryUnit = getPeriodUnit(value?.repeatEvery);
+
+  const onModeChange = (newMode: string) => {
+    if (newMode === 'inherit') {
+      onChange(null);
+      return;
+    }
+
+    if (newMode === 'disabled') {
+      onChange({
+        sendAfter: { disabled: true },
+        repeatEvery: { disabled: true },
+      });
+      return;
+    }
+
+    onChange({
+      sendAfter: { unit: sendAfterUnit, amount: sendAfterAmount },
+      repeatEvery: { unit: repeatEveryUnit, amount: repeatEveryAmount },
+    });
+  };
+
+  const updateSendAfter = (
+    updates: Partial<{ amount: number; unit: TEnvelopeReminderDurationPeriod['unit'] }>,
+  ) => {
+    const newAmount = Math.max(1, Math.floor(updates.amount ?? sendAfterAmount));
+    const newUnit = updates.unit ?? sendAfterUnit;
+
+    onChange({
+      sendAfter: { unit: newUnit, amount: newAmount },
+      repeatEvery: value?.repeatEvery ?? { unit: repeatEveryUnit, amount: repeatEveryAmount },
+    });
+  };
+
+  const updateRepeatEvery = (
+    updates: Partial<{ amount: number; unit: TEnvelopeReminderDurationPeriod['unit'] }>,
+  ) => {
+    const newAmount = Math.max(1, Math.floor(updates.amount ?? repeatEveryAmount));
+    const newUnit = updates.unit ?? repeatEveryUnit;
+
+    onChange({
+      sendAfter: value?.sendAfter ?? { unit: sendAfterUnit, amount: sendAfterAmount },
+      repeatEvery: { unit: newUnit, amount: newAmount },
+    });
+  };
+
+  const onRepeatModeChange = (newMode: string) => {
+    if (newMode === 'disabled') {
+      onChange({
+        sendAfter: value?.sendAfter ?? { unit: sendAfterUnit, amount: sendAfterAmount },
+        repeatEvery: { disabled: true },
+      });
+      return;
+    }
+
+    onChange({
+      sendAfter: value?.sendAfter ?? { unit: sendAfterUnit, amount: sendAfterAmount },
+      repeatEvery: { unit: repeatEveryUnit, amount: repeatEveryAmount },
+    });
+  };
+
+  const repeatMode = value?.repeatEvery && 'disabled' in value.repeatEvery ? 'disabled' : 'enabled';
+
+  return (
+    <div className="flex flex-col gap-4" data-testid="reminder-settings-picker">
+      <Select value={mode} onValueChange={onModeChange} disabled={disabled}>
+        <SelectTrigger className="bg-background" data-testid="reminder-mode-select">
+          <SelectValue />
+        </SelectTrigger>
+
+        <SelectContent>
+          <SelectItem value="enabled">
+            <Trans>Enabled</Trans>
+          </SelectItem>
+
+          <SelectItem value="disabled">
+            <Trans>No reminders</Trans>
+          </SelectItem>
+
+          {inheritLabel !== undefined && <SelectItem value="inherit">{inheritLabel}</SelectItem>}
+        </SelectContent>
+      </Select>
+
+      {mode === 'enabled' && (
+        <div className="flex flex-col gap-4">
+          <div className="flex flex-col gap-2">
+            <Label className="text-sm text-muted-foreground">
+              <Trans>Send first reminder after</Trans>
+            </Label>
+
+            <div className="flex flex-row gap-2">
+              <Input
+                type="number"
+                min={1}
+                className="w-20 bg-background"
+                value={sendAfterAmount}
+                onChange={(e) => updateSendAfter({ amount: Number(e.target.value) })}
+                disabled={disabled}
+                data-testid="reminder-send-after-amount"
+              />
+
+              <UnitSelect
+                value={sendAfterUnit}
+                amount={sendAfterAmount}
+                onChange={(unit) =>
+                  updateSendAfter({
+                    unit: unit as TEnvelopeReminderDurationPeriod['unit'],
+                  })
+                }
+                disabled={disabled}
+                testId="reminder-send-after-unit"
+              />
+            </div>
+          </div>
+
+          <div className="flex flex-col gap-2">
+            <Label className="text-sm text-muted-foreground">
+              <Trans>Then repeat every</Trans>
+            </Label>
+
+            <Select value={repeatMode} onValueChange={onRepeatModeChange} disabled={disabled}>
+              <SelectTrigger className="bg-background" data-testid="reminder-repeat-mode-select">
+                <SelectValue />
+              </SelectTrigger>
+
+              <SelectContent>
+                <SelectItem value="enabled">
+                  <Trans>Custom interval</Trans>
+                </SelectItem>
+
+                <SelectItem value="disabled">
+                  <Trans>Don't repeat</Trans>
+                </SelectItem>
+              </SelectContent>
+            </Select>
+
+            {repeatMode === 'enabled' && (
+              <div className="flex flex-row gap-2">
+                <Input
+                  type="number"
+                  min={1}
+                  className="w-20 bg-background"
+                  value={repeatEveryAmount}
+                  onChange={(e) => updateRepeatEvery({ amount: Number(e.target.value) })}
+                  disabled={disabled}
+                  data-testid="reminder-repeat-amount"
+                />
+
+                <UnitSelect
+                  value={repeatEveryUnit}
+                  amount={repeatEveryAmount}
+                  onChange={(unit) =>
+                    updateRepeatEvery({
+                      unit: unit as TEnvelopeReminderDurationPeriod['unit'],
+                    })
+                  }
+                  disabled={disabled}
+                  testId="reminder-repeat-unit"
+                />
+              </div>
+            )}
+          </div>
+        </div>
+      )}
+    </div>
+  );
+};
+
+const UnitSelect = ({
+  value,
+  amount,
+  onChange,
+  disabled,
+  testId,
+}: {
+  value: string;
+  amount: number;
+  onChange: (value: string) => void;
+  disabled: boolean;
+  testId: string;
+}) => (
+  <Select value={value} onValueChange={onChange} disabled={disabled}>
+    <SelectTrigger className="flex-1 bg-background" data-testid={testId}>
+      <SelectValue />
+    </SelectTrigger>
+
+    <SelectContent>
+      <SelectItem value="day">
+        <Plural value={amount} one="Day" other="Days" />
+      </SelectItem>
+      <SelectItem value="week">
+        <Plural value={amount} one="Week" other="Weeks" />
+      </SelectItem>
+      <SelectItem value="month">
+        <Plural value={amount} one="Month" other="Months" />
+      </SelectItem>
+    </SelectContent>
+  </Select>
+);

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

@@ -4,7 +4,7 @@ import { zodResolver } from '@hookform/resolvers/zod';
 import { msg } from '@lingui/core/macro';
 import { useLingui } from '@lingui/react';
 import { Trans } from '@lingui/react/macro';
-import type { Field, Recipient } from '@prisma/client';
+import type { Field } from '@prisma/client';
 import { FieldType, Prisma, RecipientRole, SendStatus } from '@prisma/client';
 import {
   CalendarDays,
@@ -28,6 +28,7 @@ import {
   type TFieldMetaSchema as FieldMeta,
   ZFieldMetaSchema,
 } from '@documenso/lib/types/field-meta';
+import type { TRecipientLite } from '@documenso/lib/types/recipient';
 import { nanoid } from '@documenso/lib/universal/id';
 import { ADVANCED_FIELD_TYPES_WITH_OPTIONAL_SETTING } from '@documenso/lib/utils/advanced-fields-helpers';
 import { validateFieldsUninserted } from '@documenso/lib/utils/fields';
@@ -83,7 +84,7 @@ export type FieldFormType = {
 export type AddFieldsFormProps = {
   documentFlow: DocumentFlowStep;
   hideRecipients?: boolean;
-  recipients: Recipient[];
+  recipients: TRecipientLite[];
   fields: Field[];
   onSubmit: (_data: TAddFieldsFormSchema) => void;
   onAutoSave: (_data: TAddFieldsFormSchema) => Promise<void>;
@@ -172,7 +173,7 @@ export const AddFieldsFormPartial = ({
   });
 
   const [selectedField, setSelectedField] = useState<FieldType | null>(null);
-  const [selectedSigner, setSelectedSigner] = useState<Recipient | null>(null);
+  const [selectedSigner, setSelectedSigner] = useState<TRecipientLite | null>(null);
   const [lastActiveField, setLastActiveField] = useState<TAddFieldsFormSchema['fields'][0] | null>(
     null,
   );
@@ -536,7 +537,7 @@ export const AddFieldsFormPartial = ({
   }, [recipients]);
 
   const recipientsByRole = useMemo(() => {
-    const recipientsByRole: Record<RecipientRole, Recipient[]> = {
+    const recipientsByRole: Record<RecipientRole, TRecipientLite[]> = {
       CC: [],
       VIEWER: [],
       SIGNER: [],

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

@@ -6,7 +6,6 @@ import {
   DocumentStatus,
   DocumentVisibility,
   type Field,
-  type Recipient,
   SendStatus,
   TeamMemberRole,
 } from '@prisma/client';
@@ -21,6 +20,7 @@ import { DOCUMENT_SIGNATURE_TYPES } from '@documenso/lib/constants/document';
 import { SUPPORTED_LANGUAGES } from '@documenso/lib/constants/i18n';
 import { DEFAULT_DOCUMENT_TIME_ZONE, TIME_ZONES } from '@documenso/lib/constants/time-zones';
 import type { TDocument } from '@documenso/lib/types/document';
+import type { TRecipientLite } from '@documenso/lib/types/recipient';
 import { extractDocumentAuthMethods } from '@documenso/lib/utils/document-auth';
 import { extractTeamSignatureSettings } from '@documenso/lib/utils/teams';
 import {
@@ -74,7 +74,7 @@ import type { DocumentFlowStep } from './types';
 
 export type AddSettingsFormProps = {
   documentFlow: DocumentFlowStep;
-  recipients: Recipient[];
+  recipients: TRecipientLite[];
   fields: Field[];
   isDocumentPdfLoaded: boolean;
   document: TDocument;

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

@@ -6,7 +6,7 @@ import { zodResolver } from '@hookform/resolvers/zod';
 import { msg } from '@lingui/core/macro';
 import { useLingui } from '@lingui/react';
 import { Trans } from '@lingui/react/macro';
-import type { Field, Recipient } from '@prisma/client';
+import type { Field } from '@prisma/client';
 import { DocumentSigningOrder, RecipientRole, SendStatus } from '@prisma/client';
 import { motion } from 'framer-motion';
 import { GripVerticalIcon, HelpCircle, Plus, Trash } from 'lucide-react';
@@ -19,6 +19,7 @@ import { useDebouncedValue } from '@documenso/lib/client-only/hooks/use-debounce
 import { useCurrentOrganisation } from '@documenso/lib/client-only/providers/organisation';
 import { useSession } from '@documenso/lib/client-only/providers/session';
 import { ZRecipientAuthOptionsSchema } from '@documenso/lib/types/document-auth';
+import type { TRecipientLite } from '@documenso/lib/types/recipient';
 import { nanoid } from '@documenso/lib/universal/id';
 import { canRecipientBeModified as utilCanRecipientBeModified } from '@documenso/lib/utils/recipients';
 import { trpc } from '@documenso/trpc/react';
@@ -54,12 +55,12 @@ import { SigningOrderConfirmation } from './signing-order-confirmation';
 import type { DocumentFlowStep } from './types';
 
 type AutoSaveResponse = {
-  recipients: Recipient[];
+  recipients: TRecipientLite[];
 };
 
 export type AddSignersFormProps = {
   documentFlow: DocumentFlowStep;
-  recipients: Recipient[];
+  recipients: TRecipientLite[];
   fields: Field[];
   signingOrder?: DocumentSigningOrder | null;
   allowDictateNextSigner?: boolean;

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

@@ -4,7 +4,7 @@ import { zodResolver } from '@hookform/resolvers/zod';
 import { msg } from '@lingui/core/macro';
 import { useLingui } from '@lingui/react';
 import { Trans } from '@lingui/react/macro';
-import type { Field, Recipient } from '@prisma/client';
+import type { Field } from '@prisma/client';
 import { DocumentDistributionMethod, DocumentStatus, RecipientRole } from '@prisma/client';
 import { AnimatePresence, motion } from 'framer-motion';
 import { InfoIcon } from 'lucide-react';
@@ -15,6 +15,7 @@ import { useCurrentOrganisation } from '@documenso/lib/client-only/providers/org
 import { RECIPIENT_ROLES_DESCRIPTION } from '@documenso/lib/constants/recipient-roles';
 import type { TDocument } from '@documenso/lib/types/document';
 import { ZDocumentEmailSettingsSchema } from '@documenso/lib/types/document-email';
+import type { TRecipientLite } from '@documenso/lib/types/recipient';
 import { formatSigningLink } from '@documenso/lib/utils/recipients';
 import { trpc } from '@documenso/trpc/react';
 import { DocumentSendEmailMessageHelper } from '@documenso/ui/components/document/document-send-email-message-helper';
@@ -59,7 +60,7 @@ import type { DocumentFlowStep } from './types';
 
 export type AddSubjectFormProps = {
   documentFlow: DocumentFlowStep;
-  recipients: Recipient[];
+  recipients: TRecipientLite[];
   fields: Field[];
   document: TDocument;
   onSubmit: (_data: TAddSubjectFormSchema) => void;

packages/ui/primitives/recipient-selector.tsx

@@ -2,12 +2,12 @@ import { useCallback, useMemo, useState } from 'react';
 
 import { useLingui } from '@lingui/react';
 import { Trans } from '@lingui/react/macro';
-import type { Recipient } from '@prisma/client';
 import { RecipientRole, SendStatus, SigningStatus } from '@prisma/client';
 import { Check, ChevronsUpDown, Info } from 'lucide-react';
 import { sortBy } from 'remeda';
 
 import { RECIPIENT_ROLES_DESCRIPTION } from '@documenso/lib/constants/recipient-roles';
+import type { TRecipientLite } from '@documenso/lib/types/recipient';
 
 import { getRecipientColorStyles } from '../lib/recipient-colors';
 import { cn } from '../lib/utils';
@@ -18,9 +18,9 @@ import { Tooltip, TooltipContent, TooltipTrigger } from './tooltip';
 
 export interface RecipientSelectorProps {
   className?: string;
-  selectedRecipient: Recipient | null;
-  onSelectedRecipientChange: (recipient: Recipient) => void;
-  recipients: Recipient[];
+  selectedRecipient: TRecipientLite | null;
+  onSelectedRecipientChange: (recipient: TRecipientLite) => void;
+  recipients: TRecipientLite[];
   align?: 'center' | 'end' | 'start';
 }
 
@@ -35,7 +35,7 @@ export const RecipientSelector = ({
   const [showRecipientsSelector, setShowRecipientsSelector] = useState(false);
 
   const recipientsByRole = useMemo(() => {
-    const recipientsWithRole: Record<RecipientRole, Recipient[]> = {
+    const recipientsWithRole: Record<RecipientRole, TRecipientLite[]> = {
       CC: [],
       VIEWER: [],
       SIGNER: [],
@@ -67,12 +67,12 @@ export const RecipientSelector = ({
               [(r) => r.signingOrder || Number.MAX_SAFE_INTEGER, 'asc'],
               [(r) => r.id, 'asc'],
             ),
-          ] as [RecipientRole, Recipient[]],
+          ] as [RecipientRole, TRecipientLite[]],
       );
   }, [recipientsByRole]);
 
   const getRecipientLabel = useCallback(
-    (recipient: Recipient) => {
+    (recipient: TRecipientLite) => {
       if (recipient.name && recipient.email) {
         return `${recipient.name} (${recipient.email})`;
       }

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

@@ -4,7 +4,7 @@ import { zodResolver } from '@hookform/resolvers/zod';
 import { msg } from '@lingui/core/macro';
 import { useLingui } from '@lingui/react';
 import { Trans } from '@lingui/react/macro';
-import type { Field, Recipient } from '@prisma/client';
+import type { Field } from '@prisma/client';
 import { FieldType, RecipientRole, SendStatus } from '@prisma/client';
 import {
   CalendarDays,
@@ -31,6 +31,7 @@ import {
   type TFieldMetaSchema as FieldMeta,
   ZFieldMetaSchema,
 } from '@documenso/lib/types/field-meta';
+import type { TRecipientLite } from '@documenso/lib/types/recipient';
 import { nanoid } from '@documenso/lib/universal/id';
 import { ADVANCED_FIELD_TYPES_WITH_OPTIONAL_SETTING } from '@documenso/lib/utils/advanced-fields-helpers';
 import { parseMessageDescriptor } from '@documenso/lib/utils/i18n';
@@ -75,7 +76,7 @@ const DEFAULT_WIDTH_PX = MIN_WIDTH_PX * 2.5;
 
 export type AddTemplateFieldsFormProps = {
   documentFlow: DocumentFlowStep;
-  recipients: Recipient[];
+  recipients: TRecipientLite[];
   fields: Field[];
   onSubmit: (_data: TAddTemplateFieldsFormSchema) => void;
   onAutoSave: (_data: TAddTemplateFieldsFormSchema) => Promise<void>;
@@ -154,7 +155,7 @@ export const AddTemplateFieldsFormPartial = ({
   });
 
   const [selectedField, setSelectedField] = useState<FieldType | null>(null);
-  const [selectedSigner, setSelectedSigner] = useState<Recipient | null>(null);
+  const [selectedSigner, setSelectedSigner] = useState<TRecipientLite | null>(null);
   const [showRecipientsSelector, setShowRecipientsSelector] = useState(false);
 
   const selectedSignerIndex = recipients.findIndex((r) => r.id === selectedSigner?.id);
@@ -491,7 +492,7 @@ export const AddTemplateFieldsFormPartial = ({
   }, [recipients]);
 
   const recipientsByRole = useMemo(() => {
-    const recipientsByRole: Record<RecipientRole, Recipient[]> = {
+    const recipientsByRole: Record<RecipientRole, TRecipientLite[]> = {
       CC: [],
       VIEWER: [],
       SIGNER: [],
@@ -520,7 +521,7 @@ export const AddTemplateFieldsFormPartial = ({
 
   const recipientsByRoleToDisplay = useMemo(() => {
     // eslint-disable-next-line @typescript-eslint/consistent-type-assertions
-    return (Object.entries(recipientsByRole) as [RecipientRole, Recipient[]][]).filter(
+    return (Object.entries(recipientsByRole) as [RecipientRole, TRecipientLite[]][]).filter(
       ([role]) =>
         role !== RecipientRole.CC &&
         role !== RecipientRole.VIEWER &&

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

@@ -7,7 +7,7 @@ import { msg } from '@lingui/core/macro';
 import { useLingui } from '@lingui/react';
 import { Trans } from '@lingui/react/macro';
 import type { TemplateDirectLink } from '@prisma/client';
-import { DocumentSigningOrder, type Field, type Recipient, RecipientRole } from '@prisma/client';
+import { DocumentSigningOrder, type Field, RecipientRole } from '@prisma/client';
 import { motion } from 'framer-motion';
 import { GripVerticalIcon, HelpCircle, Link2Icon, Plus, Trash } from 'lucide-react';
 import { useFieldArray, useForm } from 'react-hook-form';
@@ -17,6 +17,7 @@ import { useCurrentOrganisation } from '@documenso/lib/client-only/providers/org
 import { useSession } from '@documenso/lib/client-only/providers/session';
 import { isTemplateRecipientEmailPlaceholder } from '@documenso/lib/constants/template';
 import { ZRecipientAuthOptionsSchema } from '@documenso/lib/types/document-auth';
+import type { TRecipientLite } from '@documenso/lib/types/recipient';
 import { nanoid } from '@documenso/lib/universal/id';
 import { generateRecipientPlaceholder } from '@documenso/lib/utils/templates';
 import { AnimateGenericFadeInOut } from '@documenso/ui/components/animate/animate-generic-fade-in-out';
@@ -49,12 +50,12 @@ import type { TAddTemplatePlacholderRecipientsFormSchema } from './add-template-
 import { ZAddTemplatePlacholderRecipientsFormSchema } from './add-template-placeholder-recipients.types';
 
 type AutoSaveResponse = {
-  recipients: Recipient[];
+  recipients: TRecipientLite[];
 };
 
 export type AddTemplatePlaceholderRecipientsFormProps = {
   documentFlow: DocumentFlowStep;
-  recipients: Recipient[];
+  recipients: TRecipientLite[];
   fields: Field[];
   signingOrder?: DocumentSigningOrder | null;
   allowDictateNextSigner?: boolean;

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

@@ -3,7 +3,7 @@ import { useEffect } from 'react';
 import { zodResolver } from '@hookform/resolvers/zod';
 import { Trans, useLingui } from '@lingui/react/macro';
 import { DocumentVisibility, TeamMemberRole, TemplateType } from '@prisma/client';
-import { DocumentDistributionMethod, type Field, type Recipient } from '@prisma/client';
+import { DocumentDistributionMethod, type Field } from '@prisma/client';
 import { InfoIcon } from 'lucide-react';
 import { useForm } from 'react-hook-form';
 import { match } from 'ts-pattern';
@@ -19,6 +19,7 @@ import { SUPPORTED_LANGUAGES } from '@documenso/lib/constants/i18n';
 import { DEFAULT_DOCUMENT_TIME_ZONE, TIME_ZONES } from '@documenso/lib/constants/time-zones';
 import { ZDocumentEmailSettingsSchema } from '@documenso/lib/types/document-email';
 import type { TDocumentMetaDateFormat } from '@documenso/lib/types/document-meta';
+import type { TRecipientLite } from '@documenso/lib/types/recipient';
 import type { TTemplate } from '@documenso/lib/types/template';
 import { extractDocumentAuthMethods } from '@documenso/lib/utils/document-auth';
 import { extractTeamSignatureSettings } from '@documenso/lib/utils/teams';
@@ -81,7 +82,7 @@ import { ZAddTemplateSettingsFormSchema } from './add-template-settings.types';
 
 export type AddTemplateSettingsFormProps = {
   documentFlow: DocumentFlowStep;
-  recipients: Recipient[];
+  recipients: TRecipientLite[];
   fields: Field[];
   isDocumentPdfLoaded: boolean;
   template: TTemplate;