Fix threaded draft email replies (#22175)

## Summary Fixes Gmail and Microsoft draft replies so workflow-created drafts stay attached to the existing provider thread. Fixes twentyhq/core-team-issues#2597. ## Root cause The email composer already resolved `threadExternalId` and `references` from `inReplyTo`, but `DraftEmailTool` only forwarded `inReplyTo` to the outbound draft service. Gmail therefore created a raw draft without `message.threadId`, which lets the draft appear as a standalone compose instead of an inline thread reply. For Microsoft, the draft path used Graph `createReply`, but parent lookup filtered on a URL-encoded `internetMessageId`. That can miss the parent message and fall back to creating a new draft message instead of a reply draft. ## Changes - Forward `threadExternalId` and `references` from `DraftEmailTool` to outbound draft creation. - Set Gmail draft `message.threadId` when `threadExternalId` is available. - Make Microsoft parent lookup use Graph request query builders with OData string escaping, so `createReply` is reached reliably. - Add targeted Jest coverage for the Draft Email tool, Gmail draft threading, and Microsoft reply-draft creation. ## Validation - `NX_DAEMON=false /Users/thomascolasdesfrancs/.cache/codex-runtimes/codex-primary-runtime/dependencies/node/bin/node ../../node_modules/nx/dist/bin/nx.js jest twenty-server -- --runTestsByPath src/engine/core-modules/tool/tools/email-tool/__tests__/draft-email-tool.spec.ts src/modules/messaging/message-outbound-manager/drivers/gmail/services/__tests__/gmail-message-outbound.service.spec.ts src/modules/messaging/message-outbound-manager/drivers/microsoft/services/__tests__/microsoft-message-outbound.service.spec.ts --runInBand` - `NX_DAEMON=false /Users/thomascolasdesfrancs/.cache/codex-runtimes/codex-primary-runtime/dependencies/node/bin/node ./node_modules/nx/dist/bin/nx.js lint:diff-with-main twenty-server`  <a href="https://cubic.dev/pr/twentyhq/twenty/pull/22175?utm_source=github" target="_blank" rel="noopener noreferrer" data-no-image-dialog="true"><picture><source media="(prefers-color-scheme: dark)" srcset="https://www.cubic.dev/buttons/review-in-cubic-dark.svg"><source media="(prefers-color-scheme: light)" srcset="https://www.cubic.dev/buttons/review-in-cubic-light.svg"><img alt="Review in cubic" src="https://www.cubic.dev/buttons/review-in-cubic-dark.svg"></picture></a>  --------- Co-authored-by: claude[bot] <41898282+claude[bot]@users.noreply.github.com> Co-authored-by: Félix Malfait <FelixMalfait@users.noreply.github.com>
2026-06-25 18:39:01 +02:00
parent 1076866820
commit eedd838189
6 changed files with 190 additions and 8 deletions
@@ -79,13 +79,20 @@ describe('DraftEmailTool', () => {
  });

  it('creates the draft when the resolved account has the compose scope', async () => {
-    mockComposeEmail.mockResolvedValue({
-      success: true,
-      data: buildComposedEmail({
+    const composedEmail = {
+      ...buildComposedEmail({
        id: 'account-1',
        provider: ConnectedAccountProvider.GOOGLE,
        scopes: [GMAIL_COMPOSE_SCOPE],
      }),
+      inReplyTo: '<parent@example.com>',
+      threadExternalId: 'thread-external-id',
+      references: ['<ancestor@example.com>', '<parent@example.com>'],
+    };
+
+    mockComposeEmail.mockResolvedValue({
+      success: true,
+      data: composedEmail,
    });

    const result = await tool.execute(baseInput, {
@@ -94,5 +101,13 @@ describe('DraftEmailTool', () => {

    expect(result.success).toBe(true);
    expect(mockCreateDraft).toHaveBeenCalledTimes(1);
+    expect(mockCreateDraft).toHaveBeenCalledWith(
+      expect.objectContaining({
+        inReplyTo: composedEmail.inReplyTo,
+        threadExternalId: composedEmail.threadExternalId,
+        references: composedEmail.references,
+      }),
+      composedEmail.connectedAccount,
+    );
  });
 });
@@ -114,6 +114,8 @@ export class DraftEmailTool implements Tool {
        html: data.sanitizedHtmlBody,
        attachments: data.attachments,
        inReplyTo: data.inReplyTo,
+        threadExternalId: data.threadExternalId,
+        references: data.references,
      },
      data.connectedAccount,
    );
@@ -18,12 +18,18 @@ describe('GmailMessageOutboundService', () => {
  let service: GmailMessageOutboundService;

  const mockSend = jest.fn().mockResolvedValue({ data: { id: 'message-id' } });
+  const mockCreateDraft = jest
+    .fn()
+    .mockResolvedValue({ data: { id: 'draft-id' } });

  const mockGmailClient = {
    users: {
      messages: {
        send: mockSend,
      },
+      drafts: {
+        create: mockCreateDraft,
+      },
      getProfile: jest
        .fn()
        .mockResolvedValue({ data: { emailAddress: 'test@example.com' } }),
@@ -69,6 +75,7 @@ describe('GmailMessageOutboundService', () => {

  afterEach(() => {
    mockSend.mockClear();
+    mockCreateDraft.mockClear();
    jest.restoreAllMocks();
  });

@@ -127,4 +134,34 @@ describe('GmailMessageOutboundService', () => {
      },
    });
  });
+
+  it('should create Gmail drafts in the existing thread when a thread id is provided', async () => {
+    const sendMessageInput = {
+      to: 'recipient@example.com',
+      subject: 'Re: Existing thread',
+      body: 'Plain text',
+      html: '<p>HTML content</p>',
+      attachments: [],
+      inReplyTo: '<parent@example.com>',
+      threadExternalId: 'gmail-thread-id',
+    };
+
+    const connectedAccount = {
+      id: 'connected-account-id',
+      provider: ConnectedAccountProvider.GOOGLE,
+    } as any;
+
+    await service.createDraft(sendMessageInput, connectedAccount);
+
+    expect(mockCreateDraft).toHaveBeenCalledTimes(1);
+    expect(mockCreateDraft).toHaveBeenCalledWith({
+      userId: 'me',
+      requestBody: {
+        message: {
+          raw: Buffer.from('mocked-email-content').toString('base64url'),
+          threadId: 'gmail-thread-id',
+        },
+      },
+    });
+  });
 });
@@ -1,5 +1,6 @@
 import { Injectable } from '@nestjs/common';

+import { isNonEmptyString } from '@sniptt/guards';
 import { type gmail_v1, google } from 'googleapis';
 import MailComposer from 'nodemailer/lib/mail-composer';
 import { isDefined } from 'twenty-shared/utils';
@@ -31,7 +32,7 @@ export class GmailMessageOutboundService implements MessageOutboundDriver {
      userId: 'me',
      requestBody: {
        raw: encodedMessage,
-        ...(sendMessageInput.threadExternalId
+        ...(isNonEmptyString(sendMessageInput.threadExternalId)
          ? { threadId: sendMessageInput.threadExternalId }
          : {}),
      },
@@ -58,6 +59,9 @@ export class GmailMessageOutboundService implements MessageOutboundDriver {
      requestBody: {
        message: {
          raw: encodedMessage,
+          ...(isNonEmptyString(sendMessageInput.threadExternalId)
+            ? { threadId: sendMessageInput.threadExternalId }
+            : {}),
        },
      },
    });
@@ -0,0 +1,123 @@
+import { Test, type TestingModule } from '@nestjs/testing';
+
+import { ConnectedAccountProvider } from 'twenty-shared/types';
+
+import { MicrosoftOAuth2ClientProvider } from 'src/modules/connected-account/oauth2-client-manager/drivers/microsoft/microsoft-oauth2-client.provider';
+import { MicrosoftMessageOutboundService } from 'src/modules/messaging/message-outbound-manager/drivers/microsoft/services/microsoft-message-outbound.service';
+
+describe('MicrosoftMessageOutboundService', () => {
+  let service: MicrosoftMessageOutboundService;
+
+  const messagesRequest = {
+    filter: jest.fn().mockReturnThis(),
+    select: jest.fn().mockReturnThis(),
+    top: jest.fn().mockReturnThis(),
+    get: jest.fn(),
+    post: jest.fn(),
+  };
+
+  const replyRequest = {
+    post: jest.fn(),
+  };
+
+  const draftRequest = {
+    patch: jest.fn(),
+  };
+
+  const mockMicrosoftClient = {
+    api: jest.fn((path: string) => {
+      switch (path) {
+        case '/me/messages':
+          return messagesRequest;
+        case '/me/messages/parent-message-id/createReply':
+          return replyRequest;
+        case '/me/messages/reply-draft-id':
+          return draftRequest;
+        default:
+          throw new Error(`Unexpected Microsoft Graph path: ${path}`);
+      }
+    }),
+  };
+
+  beforeEach(async () => {
+    jest.clearAllMocks();
+
+    messagesRequest.filter.mockReturnThis();
+    messagesRequest.select.mockReturnThis();
+    messagesRequest.top.mockReturnThis();
+    messagesRequest.get.mockResolvedValue({
+      value: [{ id: 'parent-message-id' }],
+    });
+    replyRequest.post.mockResolvedValue({
+      id: 'reply-draft-id',
+      internetMessageId: '<reply@example.com>',
+      conversationId: 'conversation-id',
+    });
+    draftRequest.patch.mockResolvedValue({
+      id: 'reply-draft-id',
+      internetMessageId: '<patched-reply@example.com>',
+      conversationId: 'conversation-id',
+    });
+
+    const module: TestingModule = await Test.createTestingModule({
+      providers: [
+        MicrosoftMessageOutboundService,
+        {
+          provide: MicrosoftOAuth2ClientProvider,
+          useValue: {
+            getClient: jest.fn().mockResolvedValue(mockMicrosoftClient),
+          },
+        },
+      ],
+    }).compile();
+
+    service = module.get<MicrosoftMessageOutboundService>(
+      MicrosoftMessageOutboundService,
+    );
+  });
+
+  it('creates Microsoft drafts as replies when a parent internet message id is provided', async () => {
+    const connectedAccount = {
+      id: 'connected-account-id',
+      provider: ConnectedAccountProvider.MICROSOFT,
+    } as any;
+
+    await service.createDraft(
+      {
+        to: 'recipient@example.com',
+        subject: 'Re: Existing thread',
+        body: 'Plain text',
+        html: '<p>HTML content</p>',
+        attachments: [],
+        inReplyTo: "<parent's-message@example.com>",
+      },
+      connectedAccount,
+    );
+
+    expect(mockMicrosoftClient.api).toHaveBeenCalledWith('/me/messages');
+    expect(messagesRequest.filter).toHaveBeenCalledWith(
+      "internetMessageId eq '<parent''s-message@example.com>'",
+    );
+    expect(messagesRequest.select).toHaveBeenCalledWith('id');
+    expect(messagesRequest.top).toHaveBeenCalledWith(1);
+
+    expect(mockMicrosoftClient.api).toHaveBeenCalledWith(
+      '/me/messages/parent-message-id/createReply',
+    );
+    expect(replyRequest.post).toHaveBeenCalledWith({});
+
+    expect(mockMicrosoftClient.api).toHaveBeenCalledWith(
+      '/me/messages/reply-draft-id',
+    );
+    expect(draftRequest.patch).toHaveBeenCalledWith(
+      expect.objectContaining({
+        subject: 'Re: Existing thread',
+        body: {
+          contentType: 'HTML',
+          content: '<p>HTML content</p>',
+        },
+      }),
+    );
+    expect(messagesRequest.post).not.toHaveBeenCalled();
+  });
+});
@@ -97,12 +97,13 @@ export class MicrosoftMessageOutboundService implements MessageOutboundDriver {
    microsoftClient: MicrosoftGraphClient,
    internetMessageId: string,
  ): Promise<string | undefined> {
-    const encodedId = encodeURIComponent(internetMessageId);
+    const escapedInternetMessageId = internetMessageId.split("'").join("''");

    const response = await microsoftClient
-      .api(
-        `/me/messages?$filter=internetMessageId eq '${encodedId}'&$select=id&$top=1`,
-      )
+      .api('/me/messages')
+      .filter(`internetMessageId eq '${escapedInternetMessageId}'`)
+      .select('id')
+      .top(1)
      .get();

    return response?.value?.[0]?.id;