chore: merge main, resolve biome formatting conflicts

Merge origin/main into feat/external-2fa-codes. Resolve formatting
conflicts caused by biome rollout; preserve both feature streams:
PR's external 2FA token + signing-session 2FA proof additions plus
main's RateLimit/RecipientExpired/signingReminders/date-auto-insert.

In complete-document-with-token.ts, drop the duplicate early
field-fetching block introduced when main moved that logic later
with date auto-insert support; keep the EXTERNAL_TWO_FACTOR_AUTH
check using derivedRecipientActionAuth.

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

@@ -1,14 +1,11 @@
-import { EnvelopeType, RecipientRole } from '@prisma/client';
-import { SendStatus, SigningStatus } from '@prisma/client';
-
 import { DOCUMENT_AUDIT_LOG_TYPE } from '@documenso/lib/types/document-audit-logs';
-import type { TRecipientAccessAuthTypes } from '@documenso/lib/types/document-auth';
-import { type TRecipientActionAuthTypes } from '@documenso/lib/types/document-auth';
+import type { TRecipientAccessAuthTypes, TRecipientActionAuthTypes } from '@documenso/lib/types/document-auth';
 import type { ApiRequestMetadata } from '@documenso/lib/universal/extract-request-metadata';
 import { nanoid } from '@documenso/lib/universal/id';
 import { createDocumentAuditLogData } from '@documenso/lib/utils/document-audit-logs';
 import { createRecipientAuthOptions } from '@documenso/lib/utils/document-auth';
 import { prisma } from '@documenso/prisma';
+import { EnvelopeType, RecipientRole, SendStatus, SigningStatus } from '@prisma/client';
 
 import { AppError, AppErrorCode } from '../../errors/app-error';
 import type { EnvelopeIdOptions } from '../../utils/envelope';
@@ -105,8 +102,7 @@ export const createEnvelopeRecipients = async ({
             signingOrder: recipient.signingOrder,
             token: nanoid(),
             sendStatus: recipient.role === RecipientRole.CC ? SendStatus.SENT : SendStatus.NOT_SENT,
-            signingStatus:
-              recipient.role === RecipientRole.CC ? SigningStatus.SIGNED : SigningStatus.NOT_SIGNED,
+            signingStatus: recipient.role === RecipientRole.CC ? SigningStatus.SIGNED : SigningStatus.NOT_SIGNED,
             authOptions,
           },
         });
@@ -136,8 +132,6 @@ export const createEnvelopeRecipients = async ({
   });
 
   return {
-    recipients: createdRecipients.map((recipient) =>
-      mapRecipientToLegacyRecipient(recipient, envelope),
-    ),
+    recipients: createdRecipients.map((recipient) => mapRecipientToLegacyRecipient(recipient, envelope)),
   };
 };

packages/lib/server-only/recipient/delete-envelope-recipient.ts

@@ -1,13 +1,11 @@
-import { createElement } from 'react';
-
-import { msg } from '@lingui/core/macro';
-import { EnvelopeType, SendStatus } from '@prisma/client';
-
 import { mailer } from '@documenso/email/mailer';
 import RecipientRemovedFromDocumentTemplate from '@documenso/email/templates/recipient-removed-from-document';
 import { DOCUMENT_AUDIT_LOG_TYPE } from '@documenso/lib/types/document-audit-logs';
 import type { ApiRequestMetadata } from '@documenso/lib/universal/extract-request-metadata';
 import { prisma } from '@documenso/prisma';
+import { msg } from '@lingui/core/macro';
+import { EnvelopeType, SendStatus } from '@prisma/client';
+import { createElement } from 'react';
 
 import { getI18nInstance } from '../../client-only/providers/i18n-server';
 import { NEXT_PUBLIC_WEBAPP_URL } from '../../constants/app';
@@ -134,9 +132,7 @@ export const deleteEnvelopeRecipient = async ({
     });
   });
 
-  const isRecipientRemovedEmailEnabled = extractDerivedDocumentEmailSettings(
-    envelope.documentMeta,
-  ).recipientRemoved;
+  const isRecipientRemovedEmailEnabled = extractDerivedDocumentEmailSettings(envelope.documentMeta).recipientRemoved;
 
   // Send email to deleted recipient.
   if (

packages/lib/server-only/recipient/get-is-recipient-turn.ts

@@ -1,6 +1,5 @@
-import { DocumentSigningOrder, EnvelopeType, SigningStatus } from '@prisma/client';
-
 import { prisma } from '@documenso/prisma';
+import { DocumentSigningOrder, EnvelopeType, SigningStatus } from '@prisma/client';
 
 export type GetIsRecipientTurnOptions = {
   token: string;

packages/lib/server-only/recipient/get-next-pending-recipient.ts

@@ -1,6 +1,5 @@
-import { EnvelopeType } from '@prisma/client';
-
 import { prisma } from '@documenso/prisma';
+import { EnvelopeType } from '@prisma/client';
 
 import { mapDocumentIdToSecondaryId } from '../../utils/envelope';
 

packages/lib/server-only/recipient/get-recipient-by-id.ts

@@ -1,6 +1,5 @@
-import { EnvelopeType } from '@prisma/client';
-
 import { prisma } from '@documenso/prisma';
+import { EnvelopeType } from '@prisma/client';
 
 import { AppError, AppErrorCode } from '../../errors/app-error';
 import { mapSecondaryIdToDocumentId, mapSecondaryIdToTemplateId } from '../../utils/envelope';
@@ -17,12 +16,7 @@ export type GetRecipientByIdOptions = {
  * Get a recipient by ID. This will also return the recipient signing token so
  * be careful when using this.
  */
-export const getRecipientById = async ({
-  recipientId,
-  userId,
-  teamId,
-  type,
-}: GetRecipientByIdOptions) => {
+export const getRecipientById = async ({ recipientId, userId, teamId, type }: GetRecipientByIdOptions) => {
   const recipient = await prisma.recipient.findFirst({
     where: {
       id: recipientId,
@@ -48,14 +42,8 @@ export const getRecipientById = async ({
   }
 
   const legacyId = {
-    documentId:
-      type === EnvelopeType.DOCUMENT
-        ? mapSecondaryIdToDocumentId(recipient.envelope.secondaryId)
-        : null,
-    templateId:
-      type === EnvelopeType.TEMPLATE
-        ? mapSecondaryIdToTemplateId(recipient.envelope.secondaryId)
-        : null,
+    documentId: type === EnvelopeType.DOCUMENT ? mapSecondaryIdToDocumentId(recipient.envelope.secondaryId) : null,
+    templateId: type === EnvelopeType.TEMPLATE ? mapSecondaryIdToTemplateId(recipient.envelope.secondaryId) : null,
   };
 
   // Backwards compatibility mapping.

packages/lib/server-only/recipient/get-recipient-suggestions.ts

@@ -1,7 +1,6 @@
-import { EnvelopeType, Prisma } from '@prisma/client';
-
 import { buildTeamWhereQuery } from '@documenso/lib/utils/teams';
 import { prisma } from '@documenso/prisma';
+import { EnvelopeType, Prisma } from '@prisma/client';
 
 export type GetRecipientSuggestionsOptions = {
   userId: number;
@@ -9,11 +8,7 @@ export type GetRecipientSuggestionsOptions = {
   query: string;
 };
 
-export const getRecipientSuggestions = async ({
-  userId,
-  teamId,
-  query,
-}: GetRecipientSuggestionsOptions) => {
+export const getRecipientSuggestions = async ({ userId, teamId, query }: GetRecipientSuggestionsOptions) => {
   const trimmedQuery = query.trim();
 
   const nameEmailFilter = trimmedQuery
@@ -89,9 +84,7 @@ export const getRecipientSuggestions = async ({
       take: 5,
     });
 
-    const uniqueTeamMember = teamMembers.find(
-      (member) => !recipients.some((r) => r.email === member.user.email),
-    );
+    const uniqueTeamMember = teamMembers.find((member) => !recipients.some((r) => r.email === member.user.email));
 
     if (uniqueTeamMember) {
       const teamMemberSuggestion = {

packages/lib/server-only/recipient/get-recipients-for-assistant.ts

@@ -1,6 +1,5 @@
-import { FieldType } from '@prisma/client';
-
 import { prisma } from '@documenso/prisma';
+import { FieldType } from '@prisma/client';
 
 import { AppError, AppErrorCode } from '../../errors/app-error';
 

packages/lib/server-only/recipient/get-recipients-for-document.ts

@@ -1,6 +1,5 @@
-import { EnvelopeType } from '@prisma/client';
-
 import { prisma } from '@documenso/prisma';
+import { EnvelopeType } from '@prisma/client';
 
 import { getEnvelopeWhereInput } from '../envelope/get-envelope-by-id';
 
@@ -10,11 +9,7 @@ export interface GetRecipientsForDocumentOptions {
   teamId: number;
 }
 
-export const getRecipientsForDocument = async ({
-  documentId,
-  userId,
-  teamId,
-}: GetRecipientsForDocumentOptions) => {
+export const getRecipientsForDocument = async ({ documentId, userId, teamId }: GetRecipientsForDocumentOptions) => {
   const { envelopeWhereInput } = await getEnvelopeWhereInput({
     id: {
       type: 'documentId',

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

@@ -1,27 +1,18 @@
-import { createElement } from 'react';
-
-import { msg } from '@lingui/core/macro';
-import type { Recipient } from '@prisma/client';
-import { EnvelopeType, RecipientRole } from '@prisma/client';
-import { SendStatus, SigningStatus } from '@prisma/client';
-import { isDeepEqual } from 'remeda';
-
 import { mailer } from '@documenso/email/mailer';
 import RecipientRemovedFromDocumentTemplate from '@documenso/email/templates/recipient-removed-from-document';
 import { DOCUMENT_AUDIT_LOG_TYPE } from '@documenso/lib/types/document-audit-logs';
 import type { TRecipientAccessAuthTypes } from '@documenso/lib/types/document-auth';
-import {
-  type TRecipientActionAuthTypes,
-  ZRecipientAuthOptionsSchema,
-} from '@documenso/lib/types/document-auth';
+import { type TRecipientActionAuthTypes, ZRecipientAuthOptionsSchema } from '@documenso/lib/types/document-auth';
 import type { ApiRequestMetadata } from '@documenso/lib/universal/extract-request-metadata';
 import { nanoid } from '@documenso/lib/universal/id';
-import {
-  createDocumentAuditLogData,
-  diffRecipientChanges,
-} from '@documenso/lib/utils/document-audit-logs';
+import { createDocumentAuditLogData, diffRecipientChanges } from '@documenso/lib/utils/document-audit-logs';
 import { createRecipientAuthOptions } from '@documenso/lib/utils/document-auth';
 import { prisma } from '@documenso/prisma';
+import { msg } from '@lingui/core/macro';
+import type { Recipient } from '@prisma/client';
+import { EnvelopeType, RecipientRole, SendStatus, SigningStatus } from '@prisma/client';
+import { createElement } from 'react';
+import { isDeepEqual } from 'remeda';
 
 import { getI18nInstance } from '../../client-only/providers/i18n-server';
 import { NEXT_PUBLIC_WEBAPP_URL } from '../../constants/app';
@@ -120,17 +111,13 @@ export const setDocumentRecipients = async ({
   const existingRecipients = envelope.recipients;
 
   const removedRecipients = existingRecipients.filter(
-    (existingRecipient) =>
-      !normalizedRecipients.find((recipient) => recipient.id === existingRecipient.id),
+    (existingRecipient) => !normalizedRecipients.find((recipient) => recipient.id === existingRecipient.id),
   );
 
   const linkedRecipients = normalizedRecipients.map((recipient) => {
-    const existing = existingRecipients.find(
-      (existingRecipient) => existingRecipient.id === recipient.id,
-    );
+    const existing = existingRecipients.find((existingRecipient) => existingRecipient.id === recipient.id);
 
-    const canPersistedRecipientBeModified =
-      existing && canRecipientBeModified(existing, envelope.fields);
+    const canPersistedRecipientBeModified = existing && canRecipientBeModified(existing, envelope.fields);
 
     if (
       existing &&
@@ -180,8 +167,7 @@ export const setDocumentRecipients = async ({
             signingOrder: recipient.signingOrder,
             envelopeId: envelope.id,
             sendStatus: recipient.role === RecipientRole.CC ? SendStatus.SENT : SendStatus.NOT_SENT,
-            signingStatus:
-              recipient.role === RecipientRole.CC ? SigningStatus.SIGNED : SigningStatus.NOT_SIGNED,
+            signingStatus: recipient.role === RecipientRole.CC ? SigningStatus.SIGNED : SigningStatus.NOT_SIGNED,
             authOptions,
           },
           create: {
@@ -192,8 +178,7 @@ export const setDocumentRecipients = async ({
             token: nanoid(),
             envelopeId: envelope.id,
             sendStatus: recipient.role === RecipientRole.CC ? SendStatus.SENT : SendStatus.NOT_SENT,
-            signingStatus:
-              recipient.role === RecipientRole.CC ? SigningStatus.SIGNED : SigningStatus.NOT_SIGNED,
+            signingStatus: recipient.role === RecipientRole.CC ? SigningStatus.SIGNED : SigningStatus.NOT_SIGNED,
             authOptions,
           },
         });
@@ -220,9 +205,7 @@ export const setDocumentRecipients = async ({
           recipientRole: upsertedRecipient.role,
         };
 
-        const changes = recipient._persisted
-          ? diffRecipientChanges(recipient._persisted, upsertedRecipient)
-          : [];
+        const changes = recipient._persisted ? diffRecipientChanges(recipient._persisted, upsertedRecipient) : [];
 
         // Handle recipient updated audit log.
         if (recipient._persisted && changes.length > 0) {
@@ -290,9 +273,7 @@ export const setDocumentRecipients = async ({
       });
     });
 
-    const isRecipientRemovedEmailEnabled = extractDerivedDocumentEmailSettings(
-      envelope.documentMeta,
-    ).recipientRemoved;
+    const isRecipientRemovedEmailEnabled = extractDerivedDocumentEmailSettings(envelope.documentMeta).recipientRemoved;
 
     // Send emails to deleted recipients who have emails.
     await Promise.all(
@@ -338,12 +319,8 @@ export const setDocumentRecipients = async ({
 
   // Filter out recipients that have been removed or have been updated.
   const filteredRecipients: RecipientDataWithClientId[] = existingRecipients.filter((recipient) => {
-    const isRemoved = removedRecipients.find(
-      (removedRecipient) => removedRecipient.id === recipient.id,
-    );
-    const isUpdated = persistedRecipients.find(
-      (persistedRecipient) => persistedRecipient.id === recipient.id,
-    );
+    const isRemoved = removedRecipients.find((removedRecipient) => removedRecipient.id === recipient.id);
+    const isUpdated = persistedRecipients.find((persistedRecipient) => persistedRecipient.id === recipient.id);
 
     return !isRemoved && !isUpdated;
   });

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

@@ -1,17 +1,13 @@
-import type { Recipient } from '@prisma/client';
-import { EnvelopeType, RecipientRole } from '@prisma/client';
-
 import {
   DIRECT_TEMPLATE_RECIPIENT_EMAIL,
   DIRECT_TEMPLATE_RECIPIENT_NAME,
 } from '@documenso/lib/constants/direct-templates';
 import { prisma } from '@documenso/prisma';
+import type { Recipient } from '@prisma/client';
+import { EnvelopeType, RecipientRole } from '@prisma/client';
 
 import { AppError, AppErrorCode } from '../../errors/app-error';
-import {
-  type TRecipientActionAuthTypes,
-  ZRecipientAuthOptionsSchema,
-} from '../../types/document-auth';
+import { type TRecipientActionAuthTypes, ZRecipientAuthOptionsSchema } from '../../types/document-auth';
 import { nanoid } from '../../universal/id';
 import { createRecipientAuthOptions } from '../../utils/document-auth';
 import { type EnvelopeIdOptions, mapSecondaryIdToTemplateId } from '../../utils/envelope';
@@ -21,22 +17,10 @@ export type SetTemplateRecipientsOptions = {
   userId: number;
   teamId: number;
   id: EnvelopeIdOptions;
-  recipients: {
-    id?: number;
-    email: string;
-    name: string;
-    role: RecipientRole;
-    signingOrder?: number | null;
-    actionAuth?: TRecipientActionAuthTypes[];
-  }[];
+  recipients: RecipientData[];
 };
 
-export const setTemplateRecipients = async ({
-  userId,
-  teamId,
-  id,
-  recipients,
-}: SetTemplateRecipientsOptions) => {
+export const setTemplateRecipients = async ({ userId, teamId, id, recipients }: SetTemplateRecipientsOptions) => {
   const { envelopeWhereInput } = await getEnvelopeWhereInput({
     id,
     type: EnvelopeType.TEMPLATE,
@@ -95,8 +79,7 @@ export const setTemplateRecipients = async ({
   const existingRecipients = envelope.recipients;
 
   const removedRecipients = existingRecipients.filter(
-    (existingRecipient) =>
-      !normalizedRecipients.find((recipient) => recipient.id === existingRecipient.id),
+    (existingRecipient) => !normalizedRecipients.find((recipient) => recipient.id === existingRecipient.id),
   );
 
   if (envelope.directLink !== null) {
@@ -122,9 +105,7 @@ export const setTemplateRecipients = async ({
   }
 
   const linkedRecipients = normalizedRecipients.map((recipient) => {
-    const existing = existingRecipients.find(
-      (existingRecipient) => existingRecipient.id === recipient.id,
-    );
+    const existing = existingRecipients.find((existingRecipient) => existingRecipient.id === recipient.id);
 
     return {
       ...recipient,
@@ -183,7 +164,10 @@ export const setTemplateRecipients = async ({
           });
         }
 
-        return upsertedRecipient;
+        return {
+          ...upsertedRecipient,
+          clientId: recipient.clientId,
+        };
       }),
     );
   });
@@ -199,13 +183,9 @@ export const setTemplateRecipients = async ({
   }
 
   // Filter out recipients that have been removed or have been updated.
-  const filteredRecipients: Recipient[] = existingRecipients.filter((recipient) => {
-    const isRemoved = removedRecipients.find(
-      (removedRecipient) => removedRecipient.id === recipient.id,
-    );
-    const isUpdated = persistedRecipients.find(
-      (persistedRecipient) => persistedRecipient.id === recipient.id,
-    );
+  const filteredRecipients: RecipientDataWithClientId[] = existingRecipients.filter((recipient) => {
+    const isRemoved = removedRecipients.find((removedRecipient) => removedRecipient.id === recipient.id);
+    const isUpdated = persistedRecipients.find((persistedRecipient) => persistedRecipient.id === recipient.id);
 
     return !isRemoved && !isUpdated;
   });
@@ -218,3 +198,17 @@ export const setTemplateRecipients = async ({
     })),
   };
 };
+
+type RecipientData = {
+  id?: number;
+  clientId?: string | null;
+  email: string;
+  name: string;
+  role: RecipientRole;
+  signingOrder?: number | null;
+  actionAuth?: TRecipientActionAuthTypes[];
+};
+
+type RecipientDataWithClientId = Recipient & {
+  clientId?: string | null;
+};

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

@@ -1,22 +1,15 @@
-import { EnvelopeType, RecipientRole, SendStatus, SigningStatus } from '@prisma/client';
-
 import { DOCUMENT_AUDIT_LOG_TYPE } from '@documenso/lib/types/document-audit-logs';
 import type { TRecipientAccessAuthTypes } from '@documenso/lib/types/document-auth';
-import {
-  type TRecipientActionAuthTypes,
-  ZRecipientAuthOptionsSchema,
-} from '@documenso/lib/types/document-auth';
+import { type TRecipientActionAuthTypes, ZRecipientAuthOptionsSchema } from '@documenso/lib/types/document-auth';
 import type { ApiRequestMetadata } from '@documenso/lib/universal/extract-request-metadata';
-import {
-  createDocumentAuditLogData,
-  diffRecipientChanges,
-} from '@documenso/lib/utils/document-audit-logs';
+import { createDocumentAuditLogData, diffRecipientChanges } from '@documenso/lib/utils/document-audit-logs';
 import { createRecipientAuthOptions } from '@documenso/lib/utils/document-auth';
 import { prisma } from '@documenso/prisma';
+import { EnvelopeType, RecipientRole, SendStatus, SigningStatus } from '@prisma/client';
 
 import { AppError, AppErrorCode } from '../../errors/app-error';
 import { extractLegacyIds } from '../../universal/id';
-import { type EnvelopeIdOptions } from '../../utils/envelope';
+import type { EnvelopeIdOptions } from '../../utils/envelope';
 import { mapFieldToLegacyField } from '../../utils/fields';
 import { canRecipientBeModified } from '../../utils/recipients';
 import { getEnvelopeWhereInput } from '../envelope/get-envelope-by-id';
@@ -92,9 +85,7 @@ export const updateEnvelopeRecipients = async ({
   }
 
   const recipientsToUpdate = recipients.map((recipient) => {
-    const originalRecipient = envelope.recipients.find(
-      (existingRecipient) => existingRecipient.id === recipient.id,
-    );
+    const originalRecipient = envelope.recipients.find((existingRecipient) => existingRecipient.id === recipient.id);
 
     if (!originalRecipient) {
       throw new AppError(AppErrorCode.NOT_FOUND, {
@@ -142,12 +133,8 @@ export const updateEnvelopeRecipients = async ({
             role: mergedRecipient.role,
             signingOrder: mergedRecipient.signingOrder,
             envelopeId: envelope.id,
-            sendStatus:
-              mergedRecipient.role === RecipientRole.CC ? SendStatus.SENT : SendStatus.NOT_SENT,
-            signingStatus:
-              mergedRecipient.role === RecipientRole.CC
-                ? SigningStatus.SIGNED
-                : SigningStatus.NOT_SIGNED,
+            sendStatus: mergedRecipient.role === RecipientRole.CC ? SendStatus.SENT : SendStatus.NOT_SENT,
+            signingStatus: mergedRecipient.role === RecipientRole.CC ? SigningStatus.SIGNED : SigningStatus.NOT_SIGNED,
             authOptions,
           },
           include: {
@@ -158,8 +145,7 @@ export const updateEnvelopeRecipients = async ({
         // Clear all fields if the recipient role is changed to a type that cannot have fields.
         if (
           originalRecipient.role !== updatedRecipient.role &&
-          (updatedRecipient.role === RecipientRole.CC ||
-            updatedRecipient.role === RecipientRole.VIEWER)
+          (updatedRecipient.role === RecipientRole.CC || updatedRecipient.role === RecipientRole.VIEWER)
         ) {
           await tx.field.deleteMany({
             where: {

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

@@ -0,0 +1,106 @@
+import { prisma } from '@documenso/prisma';
+import { DocumentDistributionMethod, RecipientRole, SendStatus, SigningStatus } from '@prisma/client';
+
+import { resolveNextReminderAt, ZEnvelopeReminderSettings } 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 now = new Date();
+
+  const recipients = await prisma.recipient.findMany({
+    where: {
+      envelopeId,
+      signingStatus: SigningStatus.NOT_SIGNED,
+      sendStatus: SendStatus.SENT,
+      sentAt: { not: null },
+      role: { not: RecipientRole.CC },
+      // Don't reschedule reminders for recipients whose deadline has passed.
+      OR: [{ expiresAt: null }, { expiresAt: { gt: now } }],
+    },
+    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 },
+      });
+    }),
+  );
+};