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/document/resend-document.ts

@@ -1,5 +1,12 @@
-import { createElement } from 'react';
-
+import { mailer } from '@documenso/email/mailer';
+import { DocumentInviteEmailTemplate } from '@documenso/email/templates/document-invite';
+import { resolveExpiresAt } from '@documenso/lib/constants/envelope-expiration';
+import { RECIPIENT_ROLE_TO_EMAIL_TYPE, RECIPIENT_ROLES_DESCRIPTION } from '@documenso/lib/constants/recipient-roles';
+import { DOCUMENT_AUDIT_LOG_TYPE } from '@documenso/lib/types/document-audit-logs';
+import type { ApiRequestMetadata } from '@documenso/lib/universal/extract-request-metadata';
+import { createDocumentAuditLogData } from '@documenso/lib/utils/document-audit-logs';
+import { renderCustomEmailTemplate } from '@documenso/lib/utils/render-custom-email-template';
+import { prisma } from '@documenso/prisma';
 import { msg } from '@lingui/core/macro';
 import {
   DocumentStatus,
@@ -7,29 +14,21 @@ import {
   OrganisationType,
   RecipientRole,
   SigningStatus,
+  WebhookTriggerEvents,
 } from '@prisma/client';
-
-import { mailer } from '@documenso/email/mailer';
-import { DocumentInviteEmailTemplate } from '@documenso/email/templates/document-invite';
-import {
-  RECIPIENT_ROLES_DESCRIPTION,
-  RECIPIENT_ROLE_TO_EMAIL_TYPE,
-} from '@documenso/lib/constants/recipient-roles';
-import { DOCUMENT_AUDIT_LOG_TYPE } from '@documenso/lib/types/document-audit-logs';
-import type { ApiRequestMetadata } from '@documenso/lib/universal/extract-request-metadata';
-import { createDocumentAuditLogData } from '@documenso/lib/utils/document-audit-logs';
-import { renderCustomEmailTemplate } from '@documenso/lib/utils/render-custom-email-template';
-import { prisma } from '@documenso/prisma';
+import { createElement } from 'react';
 
 import { getI18nInstance } from '../../client-only/providers/i18n-server';
 import { NEXT_PUBLIC_WEBAPP_URL } from '../../constants/app';
 import { extractDerivedDocumentEmailSettings } from '../../types/document-email';
+import { mapEnvelopeToWebhookDocumentPayload, ZWebhookDocumentSchema } from '../../types/webhook-payload';
 import { isDocumentCompleted } from '../../utils/document';
 import type { EnvelopeIdOptions } from '../../utils/envelope';
 import { isRecipientEmailValidForSending } from '../../utils/recipients';
 import { renderEmailWithI18N } from '../../utils/render-email-with-i18n';
 import { getEmailContext } from '../email/get-email-context';
 import { getEnvelopeWhereInput } from '../envelope/get-envelope-by-id';
+import { triggerWebhook } from '../webhooks/trigger/trigger-webhook';
 
 export type ResendDocumentOptions = {
   id: EnvelopeIdOptions;
@@ -39,13 +38,7 @@ export type ResendDocumentOptions = {
   requestMetadata: ApiRequestMetadata;
 };
 
-export const resendDocument = async ({
-  id,
-  userId,
-  recipients,
-  teamId,
-  requestMetadata,
-}: ResendDocumentOptions) => {
+export const resendDocument = async ({ id, userId, recipients, teamId, requestMetadata }: ResendDocumentOptions) => {
   const user = await prisma.user.findFirstOrThrow({
     where: {
       id: userId,
@@ -94,11 +87,31 @@ export const resendDocument = async ({
     throw new Error('Can not send completed document');
   }
 
+  // Refresh the expiresAt on each resent recipient.
+  const expiresAt = resolveExpiresAt(envelope.documentMeta?.envelopeExpirationPeriod ?? null);
+
   const recipientsToRemind = envelope.recipients.filter(
     (recipient) =>
-      recipients.includes(recipient.id) && recipient.signingStatus === SigningStatus.NOT_SIGNED,
+      recipients.includes(recipient.id) &&
+      recipient.signingStatus === SigningStatus.NOT_SIGNED &&
+      recipient.role !== RecipientRole.CC,
   );
 
+  // Extend the expiration deadline for recipients being resent.
+  if (expiresAt && recipientsToRemind.length > 0) {
+    await prisma.recipient.updateMany({
+      where: {
+        id: {
+          in: recipientsToRemind.map((r) => r.id),
+        },
+      },
+      data: {
+        expiresAt,
+        expirationNotifiedAt: null,
+      },
+    });
+  }
+
   const isRecipientSigningRequestEmailEnabled = extractDerivedDocumentEmailSettings(
     envelope.documentMeta,
   ).recipientSigningRequest;
@@ -107,15 +120,14 @@ export const resendDocument = async ({
     return envelope;
   }
 
-  const { branding, emailLanguage, organisationType, senderEmail, replyToEmail } =
-    await getEmailContext({
-      emailType: 'RECIPIENT',
-      source: {
-        type: 'team',
-        teamId: envelope.teamId,
-      },
-      meta: envelope.documentMeta,
-    });
+  const { branding, emailLanguage, organisationType, senderEmail, replyToEmail } = await getEmailContext({
+    emailType: 'RECIPIENT',
+    source: {
+      type: 'team',
+      teamId: envelope.teamId,
+    },
+    meta: envelope.documentMeta,
+  });
 
   await Promise.all(
     recipientsToRemind.map(async (recipient) => {
@@ -130,9 +142,7 @@ export const resendDocument = async ({
       const { email, name } = recipient;
       const selfSigner = email === user.email;
 
-      const recipientActionVerb = i18n
-        ._(RECIPIENT_ROLES_DESCRIPTION[recipient.role].actionVerb)
-        .toLowerCase();
+      const recipientActionVerb = i18n._(RECIPIENT_ROLES_DESCRIPTION[recipient.role].actionVerb).toLowerCase();
 
       let emailMessage = envelope.documentMeta.message || '';
       let emailSubject = i18n._(msg`Reminder: Please ${recipientActionVerb} this document`);
@@ -145,9 +155,7 @@ export const resendDocument = async ({
       }
 
       if (organisationType === OrganisationType.ORGANISATION) {
-        emailSubject = i18n._(
-          msg`Reminder: ${envelope.team.name} invited you to ${recipientActionVerb} a document`,
-        );
+        emailSubject = i18n._(msg`Reminder: ${envelope.team.name} invited you to ${recipientActionVerb} a document`);
         emailMessage =
           envelope.documentMeta.message ||
           i18n._(
@@ -192,45 +200,46 @@ export const resendDocument = async ({
         }),
       ]);
 
-      await prisma.$transaction(
-        async (tx) => {
-          await mailer.sendMail({
-            to: {
-              address: email,
-              name,
-            },
-            from: senderEmail,
-            replyTo: replyToEmail,
-            subject: envelope.documentMeta.subject
-              ? renderCustomEmailTemplate(
-                  i18n._(msg`Reminder: ${envelope.documentMeta.subject}`),
-                  customEmailTemplate,
-                )
-              : emailSubject,
-            html,
-            text,
-          });
-
-          await tx.documentAuditLog.create({
-            data: createDocumentAuditLogData({
-              type: DOCUMENT_AUDIT_LOG_TYPE.EMAIL_SENT,
-              envelopeId: envelope.id,
-              metadata: requestMetadata,
-              data: {
-                emailType: recipientEmailType,
-                recipientEmail: recipient.email,
-                recipientName: recipient.name,
-                recipientRole: recipient.role,
-                recipientId: recipient.id,
-                isResending: true,
-              },
-            }),
-          });
+      // Send email outside any transaction to avoid holding a connection
+      // open during network I/O.
+      await mailer.sendMail({
+        to: {
+          address: email,
+          name,
         },
-        { timeout: 30_000 },
-      );
+        from: senderEmail,
+        replyTo: replyToEmail,
+        subject: envelope.documentMeta.subject
+          ? renderCustomEmailTemplate(i18n._(msg`Reminder: ${envelope.documentMeta.subject}`), customEmailTemplate)
+          : emailSubject,
+        html,
+        text,
+      });
+
+      await prisma.documentAuditLog.create({
+        data: createDocumentAuditLogData({
+          type: DOCUMENT_AUDIT_LOG_TYPE.EMAIL_SENT,
+          envelopeId: envelope.id,
+          metadata: requestMetadata,
+          data: {
+            emailType: recipientEmailType,
+            recipientEmail: recipient.email,
+            recipientName: recipient.name,
+            recipientRole: recipient.role,
+            recipientId: recipient.id,
+            isResending: true,
+          },
+        }),
+      });
     }),
   );
 
+  await triggerWebhook({
+    event: WebhookTriggerEvents.DOCUMENT_REMINDER_SENT,
+    data: ZWebhookDocumentSchema.parse(mapEnvelopeToWebhookDocumentPayload(envelope)),
+    userId: envelope.userId,
+    teamId: envelope.teamId,
+  });
+
   return envelope;
 };