diff --git a/packages/app-tests/e2e/recipient/signing-groups.spec.ts b/packages/app-tests/e2e/recipient/signing-groups.spec.ts
new file mode 100644
index 000000000..9b1ab89c3
--- /dev/null
+++ b/packages/app-tests/e2e/recipient/signing-groups.spec.ts
@@ -0,0 +1,95 @@
+import { prisma } from '@documenso/prisma';
+import { seedPendingDocumentWithFullFields } from '@documenso/prisma/seed/documents';
+import { seedUser } from '@documenso/prisma/seed/users';
+import type { Page } from '@playwright/test';
+import { expect, test } from '@playwright/test';
+import { DocumentSigningOrder, DocumentStatus, FieldType } from '@prisma/client';
+
+import { signSignaturePad } from '../fixtures/signature';
+
+type SeededRecipient = Awaited<ReturnType<typeof seedPendingDocumentWithFullFields>>['recipients'][number];
+
+const completeSigning = async (page: Page, recipient: SeededRecipient) => {
+  const signUrl = `/sign/${recipient.token}`;
+
+  await page.goto(signUrl);
+  await expect(page.getByRole('heading', { name: 'Sign Document' })).toBeVisible();
+
+  await signSignaturePad(page);
+
+  for (const field of recipient.fields) {
+    await page.locator(`#field-${field.id}`).getByRole('button').click();
+
+    if (field.type === FieldType.TEXT) {
+      await page.locator('#custom-text').fill('TEXT');
+      await page.getByRole('button', { name: 'Save' }).click();
+    }
+
+    await expect(page.locator(`#field-${field.id}`)).toHaveAttribute('data-inserted', 'true');
+  }
+
+  await page.getByRole('button', { name: 'Complete' }).click();
+  await page.getByRole('button', { name: 'Sign' }).click();
+  await page.waitForURL(`${signUrl}/complete`);
+};
+
+const expectWaiting = async (page: Page, token: string) => {
+  await page.goto(`/sign/${token}`);
+  await page.waitForURL(`/sign/${token}/waiting`);
+};
+
+test('[SIGNING_GROUPS]: group members sign in any order and gate the next step', async ({ page }) => {
+  const { user, team } = await seedUser();
+  const { user: signer1 } = await seedUser();
+  const { user: signer2a } = await seedUser();
+  const { user: signer2b } = await seedUser();
+  const { user: signer3 } = await seedUser();
+
+  const { recipients, document } = await seedPendingDocumentWithFullFields({
+    owner: user,
+    teamId: team.id,
+    recipients: [signer1, signer2a, signer2b, signer3],
+    recipientsCreateOptions: [{ signingOrder: 1 }, { signingOrder: 2 }, { signingOrder: 2 }, { signingOrder: 3 }],
+    updateDocumentOptions: {
+      documentMeta: {
+        upsert: {
+          create: { signingOrder: DocumentSigningOrder.SEQUENTIAL },
+          update: { signingOrder: DocumentSigningOrder.SEQUENTIAL },
+        },
+      },
+    },
+  });
+
+  const [recipient1, recipient2a, recipient2b, recipient3] = recipients;
+
+  // While step 1 is pending, both group members and step 3 are blocked.
+  await expectWaiting(page, recipient2a.token);
+  await expectWaiting(page, recipient2b.token);
+  await expectWaiting(page, recipient3.token);
+
+  await completeSigning(page, recipient1);
+
+  // The group is now active; step 3 is still blocked.
+  await expectWaiting(page, recipient3.token);
+
+  // Sign with the SECOND group member first to prove any-order signing.
+  await completeSigning(page, recipient2b);
+
+  // One group member remains — step 3 stays blocked.
+  await expectWaiting(page, recipient3.token);
+
+  await completeSigning(page, recipient2a);
+
+  // The whole group is done — step 3 unlocks and completes the document.
+  await completeSigning(page, recipient3);
+
+  await expect
+    .poll(async () => {
+      const envelope = await prisma.envelope.findUniqueOrThrow({
+        where: { id: document.id },
+      });
+
+      return envelope.status;
+    })
+    .toBe(DocumentStatus.COMPLETED);
+});