From 2f24a8eab25c050855272f513906b371fd3f5a8a Mon Sep 17 00:00:00 2001
From: David Nguyen <davidngu28@gmail.com>
Date: Mon, 22 Jun 2026 17:00:24 +1000
Subject: [PATCH] fix: set send status on resend (#3011)

---
 .../api/v2/redistribute-send-status.spec.ts   | 64 +++++++++++++++++++
 .../server-only/document/resend-document.ts   | 13 ++++
 2 files changed, 77 insertions(+)
 create mode 100644 packages/app-tests/e2e/api/v2/redistribute-send-status.spec.ts

diff --git a/packages/app-tests/e2e/api/v2/redistribute-send-status.spec.ts b/packages/app-tests/e2e/api/v2/redistribute-send-status.spec.ts
new file mode 100644
index 000000000..11bbb149b
--- /dev/null
+++ b/packages/app-tests/e2e/api/v2/redistribute-send-status.spec.ts
@@ -0,0 +1,64 @@
+import { NEXT_PUBLIC_WEBAPP_URL } from '@documenso/lib/constants/app';
+import { createApiToken } from '@documenso/lib/server-only/public-api/create-api-token';
+import { mapSecondaryIdToDocumentId } from '@documenso/lib/utils/envelope';
+import { prisma } from '@documenso/prisma';
+import { SendStatus, SigningStatus } from '@documenso/prisma/client';
+import { seedPendingDocument } from '@documenso/prisma/seed/documents';
+import { seedUser } from '@documenso/prisma/seed/users';
+import { expect, test } from '@playwright/test';
+import type { Team, User } from '@prisma/client';
+
+const WEBAPP_BASE_URL = NEXT_PUBLIC_WEBAPP_URL();
+const baseUrl = `${WEBAPP_BASE_URL}/api/v2-beta`;
+
+test.describe.configure({
+  mode: 'parallel',
+});
+
+test.describe('Redistribute updates recipient send status', () => {
+  let user: User, team: Team, token: string;
+
+  test.beforeEach(async () => {
+    ({ user, team } = await seedUser());
+    ({ token } = await createApiToken({
+      userId: user.id,
+      teamId: team.id,
+      tokenName: 'test',
+      expiresIn: null,
+    }));
+  });
+
+  test('marks a NOT_SENT signer as SENT after a successful resend', async ({ request }) => {
+    const document = await seedPendingDocument(user, team.id, ['recipient@test.documenso.com']);
+
+    const [recipient] = document.recipients;
+
+    // Simulate a recipient that is stuck at NOT_SENT on a pending document
+    // (e.g. the initial send did not dispatch an email for them).
+    await prisma.recipient.update({
+      where: { id: recipient.id },
+      data: {
+        sendStatus: SendStatus.NOT_SENT,
+        signingStatus: SigningStatus.NOT_SIGNED,
+        sentAt: null,
+      },
+    });
+
+    const res = await request.post(`${baseUrl}/document/redistribute`, {
+      headers: { Authorization: `Bearer ${token}` },
+      data: {
+        documentId: mapSecondaryIdToDocumentId(document.secondaryId),
+        recipients: [recipient.id],
+      },
+    });
+
+    expect(res.ok(), `redistribute should succeed: ${await res.text()}`).toBeTruthy();
+
+    const updatedRecipient = await prisma.recipient.findFirstOrThrow({
+      where: { id: recipient.id },
+    });
+
+    expect(updatedRecipient.sendStatus).toBe(SendStatus.SENT);
+    expect(updatedRecipient.sentAt).not.toBeNull();
+  });
+});
diff --git a/packages/lib/server-only/document/resend-document.ts b/packages/lib/server-only/document/resend-document.ts
index 050d973c7..c270199a3 100644
--- a/packages/lib/server-only/document/resend-document.ts
+++ b/packages/lib/server-only/document/resend-document.ts
@@ -13,6 +13,7 @@ import {
   EnvelopeType,
   OrganisationType,
   RecipientRole,
+  SendStatus,
   SigningStatus,
   WebhookTriggerEvents,
 } from '@prisma/client';
@@ -276,6 +277,18 @@ export const resendDocument = async ({ id, userId, recipients, teamId, requestMe
         }),
       });
 
+      // Mark the recipient as sent if they were not already sent.
+      await prisma.recipient.updateMany({
+        where: {
+          id: recipient.id,
+          sendStatus: SendStatus.NOT_SENT,
+        },
+        data: {
+          sendStatus: SendStatus.SENT,
+          sentAt: new Date(),
+        },
+      });
+
       await prisma.documentAuditLog.create({
         data: createDocumentAuditLogData({
           type: DOCUMENT_AUDIT_LOG_TYPE.EMAIL_SENT,