feat(messaging): sync draft emails and edit them in the thread composer (#22178)

Stop excluding drafts from sync across all three providers (Gmail DRAFT label, Microsoft/IMAP Drafts folder) and add an isDraft boolean field on Message so drafts are queryable by the API and AI agents. Drafts render in the thread with a Draft tag; clicking one opens the existing reply composer pre-filled with the draft's recipients, subject and body, and Send reuses the existing send-email flow.  <a href="https://cubic.dev/pr/twentyhq/twenty/pull/22178?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: Félix Malfait <felix.malfait@gmail.com>
2026-06-30 16:37:53 +05:30
parent c4a6446757
commit 9f3ebaaf22
60 changed files with 2057 additions and 1100 deletions
@@ -29,6 +29,7 @@ const createMockMessage = (
  messageCampaign: null,
  messageCampaignId: null,
  deliveryStatus: null,
+  isDraft: false,
  deletedAt: null,
  createdAt: '2024-03-20T09:00:00Z',
  updatedAt: '2024-03-20T09:00:00Z',
@@ -19,4 +19,5 @@ export class MessageWorkspaceEntity extends BaseWorkspaceEntity {
  messageCampaign: EntityRelation<MessageCampaignWorkspaceEntity> | null;
  messageCampaignId: string | null;
  deliveryStatus: string | null;
+  isDraft: boolean;
 }
@@ -1,7 +1,6 @@
 import { StandardFolder } from 'src/modules/messaging/message-import-manager/drivers/types/standard-folder';

 export const MESSAGING_FOLDER_MANAGER_ALWAYS_EXCLUDED_FOLDERS = [
-  StandardFolder.DRAFTS,
  StandardFolder.TRASH,
  StandardFolder.JUNK,
 ];
@@ -5,6 +5,7 @@ describe('shouldCreateFolderByDefault', () => {
  it('should allow creating user folders', () => {
    expect(shouldCreateFolderByDefault(StandardFolder.INBOX)).toBe(true);
    expect(shouldCreateFolderByDefault(StandardFolder.SENT)).toBe(true);
+    expect(shouldCreateFolderByDefault(StandardFolder.DRAFTS)).toBe(true);
  });

  it('should allow creating custom folders', () => {
@@ -13,7 +14,6 @@ describe('shouldCreateFolderByDefault', () => {
  });

  it('should prevent creating system-excluded folders', () => {
-    expect(shouldCreateFolderByDefault(StandardFolder.DRAFTS)).toBe(false);
    expect(shouldCreateFolderByDefault(StandardFolder.TRASH)).toBe(false);
    expect(shouldCreateFolderByDefault(StandardFolder.JUNK)).toBe(false);
  });
@@ -1,6 +1 @@
-export const MESSAGING_GMAIL_EXCLUDED_SYSTEM_LABELS = [
-  'TRASH',
-  'SPAM',
-  'DRAFT',
-  'CHAT',
-];
+export const MESSAGING_GMAIL_EXCLUDED_SYSTEM_LABELS = ['TRASH', 'SPAM', 'CHAT'];
@@ -190,8 +190,8 @@ describe('computeGmailExcludeSearchFilter', () => {

    expect(result).toContain('-label:trash');
    expect(result).toContain('-label:spam');
-    expect(result).toContain('-label:draft');
    expect(result).toContain('-label:chat');
+    expect(result).not.toContain('-label:draft');
  });

  it('uses -category: syntax for category exclusions in ALL_FOLDERS mode', () => {
@@ -152,4 +152,32 @@ describe('parseAndFormatGmailMessage', () => {

    expect(result).toBeNull();
  });
+
+  it('should keep a draft missing a Message-ID header by synthesizing a fallback id', () => {
+    const result = parseAndFormatGmailMessage(
+      buildMessage(
+        [
+          { name: 'From', value: 'me@example.com' },
+          { name: 'To', value: 'alice@example.com' },
+        ],
+        { labelIds: ['DRAFT'] },
+      ),
+      connectedAccount,
+    );
+
+    expect(result?.isDraft).toBe(true);
+    expect(result?.headerMessageId).toBe('draft-msg-1');
+  });
+
+  it('should still drop a non-draft message missing a Message-ID header', () => {
+    const result = parseAndFormatGmailMessage(
+      buildMessage([
+        { name: 'From', value: 'sender@example.com' },
+        { name: 'To', value: 'alice@example.com' },
+      ]),
+      connectedAccount,
+    );
+
+    expect(result).toBeNull();
+  });
 });
@@ -33,7 +33,18 @@ export const parseAndFormatGmailMessage = (
    labelIds,
  } = parseGmailMessage(message);

-  if (!isDefined(from) || !isDefined(headerMessageId) || !isDefined(threadId)) {
+  const isDraft = (labelIds ?? []).includes('DRAFT');
+
+  // Gmail may omit the Message-ID header on drafts; synthesize a stable id from
+  // the message id so drafts aren't dropped.
+  const resolvedHeaderMessageId =
+    headerMessageId ?? (isDraft ? `draft-${id}` : undefined);
+
+  if (
+    !isDefined(from) ||
+    !isDefined(resolvedHeaderMessageId) ||
+    !isDefined(threadId)
+  ) {
    return null;
  }

@@ -58,13 +69,13 @@ export const parseAndFormatGmailMessage = (
    (participant) => participant.role !== MessageParticipantRole.FROM,
  );

-  if (!hasRecipientParticipant) {
+  if (!hasRecipientParticipant && !isDraft) {
    return null;
  }

  return {
    externalId: id,
-    headerMessageId,
+    headerMessageId: resolvedHeaderMessageId,
    subject: subject || '',
    messageThreadExternalId: threadId,
    receivedAt: new Date(parseInt(internalDate)),
@@ -74,5 +85,6 @@ export const parseAndFormatGmailMessage = (
    attachments,
    messageFolderExternalIds: labelIds,
    labelIds,
+    isDraft,
  };
 };
@@ -145,6 +145,7 @@ export class ImapGetMessagesService {
          folderPath,
          folderExternalId,
          connectedAccount,
+          result.flags,
        ),
      );
    }
@@ -162,6 +163,7 @@ export class ImapGetMessagesService {
    folderPath: string,
    folderExternalId: string,
    connectedAccount: Pick<ConnectedAccountEntity, 'handle' | 'handleAliases'>,
+    flags?: Set<string>,
  ): MessageWithParticipants {
    const fromAddresses = extractAddressesFromParsedEmail(parsed.from);
    const senderAddress = fromAddresses[0]?.address ?? '';
@@ -184,6 +186,7 @@ export class ImapGetMessagesService {
      })),
      participants: extractParticipantsFromParsedEmail(parsed),
      messageFolderExternalIds: [folderExternalId],
+      isDraft: flags?.has('\\Draft') ?? false,
    };
  }
 }
@@ -6,6 +6,7 @@ import PostalMime, { type Email as ParsedEmail } from 'postal-mime';
 export type MessageParseResult = {
  uid: number;
  parsed: ParsedEmail | null;
+  flags?: Set<string>;
  error?: Error;
 };

@@ -40,7 +41,7 @@ export class ImapMessageParserService {

      const messages = await client.fetchAll(
        uidSet,
-        { uid: true, source: true },
+        { uid: true, source: true, flags: true },
        { uid: true },
      );

@@ -80,22 +81,22 @@ export class ImapMessageParserService {
  private async parseMessage(
    message: FetchMessageObject,
  ): Promise<MessageParseResult> {
-    const { uid, source } = message;
+    const { uid, source, flags } = message;

    if (!source) {
      this.logger.debug(`No source content for message UID ${uid}`);

-      return { uid, parsed: null };
+      return { uid, parsed: null, flags };
    }

    try {
      const parsed = await PostalMime.parse(source);

-      return { uid, parsed };
+      return { uid, parsed, flags };
    } catch (error) {
      this.logger.error(`Failed to parse message UID ${uid}: ${error.message}`);

-      return { uid, parsed: null, error: error as Error };
+      return { uid, parsed: null, flags, error: error as Error };
    }
  }

@@ -35,6 +35,7 @@ export class InboundEmailParserService {
      direction: MessageDirection.INCOMING,
      attachments: [],
      participants: extractParticipantsFromParsedEmail(parsedEmail),
+      isDraft: false,
    };
  }
 }
@@ -99,6 +99,7 @@ describe('Microsoft get messages service', () => {
          role: MessageParticipantRole.TO,
        },
      ],
+      isDraft: false,
      attachments: [],
      messageFolderExternalIds: responseExample1.body.parentFolderId
        ? [responseExample1.body.parentFolderId]
@@ -145,6 +146,7 @@ describe('Microsoft get messages service', () => {
          role: MessageParticipantRole.CC,
        },
      ],
+      isDraft: false,
      attachments: [],
      messageFolderExternalIds: responseExample2.body.parentFolderId
        ? [responseExample2.body.parentFolderId]
@@ -188,6 +190,7 @@ describe('Microsoft get messages service', () => {
          role: MessageParticipantRole.FROM,
        },
      ],
+      isDraft: false,
      attachments: [],
      messageFolderExternalIds: responseExample.body.parentFolderId
        ? [responseExample.body.parentFolderId]
@@ -163,6 +163,7 @@ export class MicrosoftGetMessagesService {
        messageFolderExternalIds: response.parentFolderId
          ? [response.parentFolderId]
          : [],
+        isDraft: response.isDraft ?? false,
      };
    });

@@ -24,6 +24,7 @@ type MessageAccumulator = {
    | 'receivedAt'
    | 'text'
    | 'messageThreadId'
+    | 'isDraft'
  >;
  threadToCreate?: Pick<MessageThreadWorkspaceEntity, 'id' | 'subject'>;
  messageChannelMessageAssociationToCreate?: Pick<
@@ -168,6 +169,7 @@ export class MessagingMessageService {
              receivedAt: message.receivedAt,
              text: message.text,
              messageThreadId,
+              isDraft: message.isDraft,
            };

            messageAccumulator.messageToCreate = messageToCreate;
@@ -55,6 +55,7 @@ describe('MessagingSaveMessagesAndEnqueueContactCreationService', () => {
      text: 'Test content 1',
      receivedAt: new Date(),
      attachments: [],
+      isDraft: false,
      messageThreadExternalId: 'thread-1',
      direction: MessageDirection.OUTGOING,
      participants: [
@@ -77,6 +78,7 @@ describe('MessagingSaveMessagesAndEnqueueContactCreationService', () => {
      text: 'Test content 2',
      receivedAt: new Date(),
      attachments: [],
+      isDraft: false,
      messageThreadExternalId: 'thread-1',
      direction: MessageDirection.INCOMING,
      participants: [
@@ -329,4 +331,40 @@ describe('MessagingSaveMessagesAndEnqueueContactCreationService', () => {
      },
    );
  });
+
+  it('should not create contacts for unsent drafts', async () => {
+    await service.saveMessagesAndEnqueueContactCreation(
+      [
+        {
+          ...mockMessages[0],
+          isDraft: true,
+          participants: [
+            {
+              role: MessageParticipantRole.FROM,
+              handle: 'test@example.com',
+              displayName: 'Test User',
+            },
+            {
+              role: MessageParticipantRole.TO,
+              handle: 'prospect@company.com',
+              displayName: 'Prospect',
+            },
+          ],
+        },
+      ],
+      mockMessageChannel,
+      mockConnectedAccount,
+      workspaceId,
+    );
+
+    expect(messageQueueService.add).toHaveBeenCalledWith(
+      CreateCompanyAndContactJob.name,
+      {
+        workspaceId,
+        connectedAccount: mockConnectedAccount,
+        source: FieldActorSource.EMAIL,
+        contactsToCreate: [],
+      },
+    );
+  });
 });
@@ -96,7 +96,10 @@ export class MessagingSaveMessagesAndEnqueueContactCreationService {
                        messageChannel.excludeNonProfessionalEmails &&
                        !isWorkEmail(participant.handle);

+                      // Drafts are outgoing, so don't turn recipients of an
+                      // unsent email into CRM contacts.
                      const shouldCreateContact =
+                        !message.isDraft &&
                        !!participant.handle &&
                        !isParticipantConnectedAccount &&
                        !isExcludedByNonProfessionalEmails &&
@@ -25,6 +25,7 @@ export const messagingGetMessagesServiceGetMessages = [
      },
    ],
    attachments: [],
+    isDraft: false,
  },
  {
    externalId: 'AA-work-emails-external',
@@ -47,6 +48,7 @@ export const messagingGetMessagesServiceGetMessages = [
      },
    ],
    attachments: [],
+    isDraft: false,
  },
  {
    externalId: 'AA-personal-emails',
@@ -69,5 +71,6 @@ export const messagingGetMessagesServiceGetMessages = [
      },
    ],
    attachments: [],
+    isDraft: false,
  },
 ] satisfies MessageWithParticipants[];
@@ -93,6 +93,7 @@ describe('filterEmails', () => {
          },
        ],
        attachments: [],
+        isDraft: false,
      },
      {
        externalId: 'support-message',
@@ -110,6 +111,7 @@ describe('filterEmails', () => {
          },
        ],
        attachments: [],
+        isDraft: false,
      },
      {
        externalId: 'regular-message',
@@ -127,6 +129,7 @@ describe('filterEmails', () => {
          },
        ],
        attachments: [],
+        isDraft: false,
      },
    ];

@@ -155,6 +158,7 @@ describe('filterEmails', () => {
          },
        ],
        attachments: [],
+        isDraft: false,
      },
    ];

@@ -176,6 +180,7 @@ describe('filterEmails', () => {
        direction: MessageDirection.INCOMING,
        participants: undefined as any,
        attachments: [],
+        isDraft: false,
      },
    ];

@@ -203,6 +208,7 @@ describe('filterEmails', () => {
          },
        ],
        attachments: [],
+        isDraft: false,
      },
    ];

@@ -236,6 +242,7 @@ describe('filterEmails', () => {
          },
        ],
        attachments: [],
+        isDraft: false,
      },
      {
        externalId: 'alias-sent-message',
@@ -258,6 +265,7 @@ describe('filterEmails', () => {
          },
        ],
        attachments: [],
+        isDraft: false,
      },
      {
        externalId: 'reply-from-john',
@@ -280,6 +288,7 @@ describe('filterEmails', () => {
          },
        ],
        attachments: [],
+        isDraft: false,
      },
      {
        externalId: 'incoming-from-noreply',
@@ -302,6 +311,7 @@ describe('filterEmails', () => {
          },
        ],
        attachments: [],
+        isDraft: false,
      },
    ];

@@ -71,6 +71,13 @@ export class EmailGroupMessageOutboundService implements MessageOutboundDriver {
    );
  }

+  async sendDraft(): Promise<SendMessageResult> {
+    throw new MessageChannelException(
+      'Email handle channels do not support drafts.',
+      MessageChannelExceptionCode.INVALID_MESSAGE_CHANNEL_INPUT,
+    );
+  }
+
  private async resolveEmailingDomain(
    connectedAccount: ConnectedAccountEntity,
  ): Promise<EmailingDomainEntity> {
@@ -1,4 +1,4 @@
-import { Injectable } from '@nestjs/common';
+import { Injectable, Logger } from '@nestjs/common';

 import { isNonEmptyString } from '@sniptt/guards';
 import { type gmail_v1, google } from 'googleapis';
@@ -17,6 +17,8 @@ import { toMailComposerOptions } from 'src/modules/messaging/message-outbound-ma

@Injectable()
 export class GmailMessageOutboundService implements MessageOutboundDriver {
+  private readonly logger = new Logger(GmailMessageOutboundService.name);
+
  constructor(
    private readonly googleOAuth2ClientProvider: GoogleOAuth2ClientProvider,
  ) {}
@@ -67,6 +69,78 @@ export class GmailMessageOutboundService implements MessageOutboundDriver {
    });
  }

+  async sendDraft(
+    draftExternalId: string,
+    sendMessageInput: SendMessageInput,
+    connectedAccount: ConnectedAccountEntity,
+  ): Promise<SendMessageResult> {
+    const sendResult = await this.sendMessage(
+      sendMessageInput,
+      connectedAccount,
+    );
+
+    try {
+      await this.deleteDraftByMessageId(connectedAccount, draftExternalId);
+    } catch (error) {
+      this.logger.warn(
+        `Failed to delete Gmail draft for message ${draftExternalId} after send: ${error}`,
+      );
+    }
+
+    return sendResult;
+  }
+
+  private async deleteDraftByMessageId(
+    connectedAccount: ConnectedAccountEntity,
+    messageId: string,
+  ): Promise<void> {
+    const oAuth2Client = await this.googleOAuth2ClientProvider.getClient(
+      connectedAccount.id,
+    );
+
+    const gmailClient = google.gmail({ version: 'v1', auth: oAuth2Client });
+
+    const draftId = await this.findDraftIdByMessageId(gmailClient, messageId);
+
+    if (isDefined(draftId)) {
+      await gmailClient.users.drafts.delete({ userId: 'me', id: draftId });
+
+      return;
+    }
+
+    this.logger.warn(
+      `No Gmail draft found for message ${messageId}; skipping delete`,
+    );
+  }
+
+  private async findDraftIdByMessageId(
+    gmailClient: gmail_v1.Gmail,
+    messageId: string,
+  ): Promise<string | undefined> {
+    let pageToken: string | undefined = undefined;
+
+    do {
+      const { data }: { data: gmail_v1.Schema$ListDraftsResponse } =
+        await gmailClient.users.drafts.list({
+          userId: 'me',
+          maxResults: 500,
+          pageToken,
+        });
+
+      const draft = (data.drafts ?? []).find(
+        (currentDraft) => currentDraft.message?.id === messageId,
+      );
+
+      if (isDefined(draft?.id)) {
+        return draft.id;
+      }
+
+      pageToken = data.nextPageToken ?? undefined;
+    } while (isDefined(pageToken));
+
+    return undefined;
+  }
+
  private async composeGmailMessage(
    connectedAccount: ConnectedAccountEntity,
    sendMessageInput: SendMessageInput,
@@ -1,4 +1,4 @@
-import { Injectable } from '@nestjs/common';
+import { Injectable, Logger } from '@nestjs/common';
 import { InjectRepository } from '@nestjs/typeorm';

 import MailComposer from 'nodemailer/lib/mail-composer';
@@ -13,6 +13,7 @@ import { type ConnectedAccountEntity } from 'src/engine/metadata-modules/connect
 import { ImapClientProvider } from 'src/modules/messaging/message-import-manager/drivers/imap/providers/imap-client.provider';
 import { ImapFindDraftsFolderService } from 'src/modules/messaging/message-import-manager/drivers/imap/services/imap-find-drafts-folder.service';
 import { getImapFolderPath } from 'src/modules/messaging/message-import-manager/drivers/imap/utils/get-imap-folder-path.util';
+import { parseMessageId } from 'src/modules/messaging/message-import-manager/drivers/imap/utils/parse-message-id.util';
 import { SmtpClientProvider } from 'src/modules/messaging/message-import-manager/drivers/smtp/providers/smtp-client.provider';
 import { type SendMessageInput } from 'src/modules/messaging/message-outbound-manager/types/send-message-input.type';
 import { type SendMessageResult } from 'src/modules/messaging/message-outbound-manager/types/send-message-result.type';
@@ -21,6 +22,8 @@ import { toMailComposerOptions } from 'src/modules/messaging/message-outbound-ma

@Injectable()
 export class ImapSmtpMessageOutboundService implements MessageOutboundDriver {
+  private readonly logger = new Logger(ImapSmtpMessageOutboundService.name);
+
  constructor(
    private readonly smtpClientProvider: SmtpClientProvider,
    private readonly imapClientProvider: ImapClientProvider,
@@ -131,6 +134,56 @@ export class ImapSmtpMessageOutboundService implements MessageOutboundDriver {
    }
  }

+  async sendDraft(
+    draftExternalId: string,
+    sendMessageInput: SendMessageInput,
+    connectedAccount: ConnectedAccountEntity,
+  ): Promise<SendMessageResult> {
+    const sendResult = await this.sendMessage(
+      sendMessageInput,
+      connectedAccount,
+    );
+
+    try {
+      await this.deleteDraft(draftExternalId, connectedAccount);
+    } catch (error) {
+      this.logger.warn(
+        `Failed to delete IMAP draft ${draftExternalId} after send: ${error}`,
+      );
+    }
+
+    return sendResult;
+  }
+
+  async deleteDraft(
+    externalId: string,
+    connectedAccount: ConnectedAccountEntity,
+  ): Promise<void> {
+    const parsedMessageId = parseMessageId(externalId);
+
+    if (!isDefined(parsedMessageId)) {
+      throw new Error(
+        `Could not resolve IMAP drafts folder and uid from external id ${externalId}`,
+      );
+    }
+
+    const imapClient = await this.imapClientProvider.getClient(
+      connectedAccount.id,
+    );
+
+    try {
+      const lock = await imapClient.getMailboxLock(parsedMessageId.folder);
+
+      try {
+        await imapClient.messageDelete(`${parsedMessageId.uid}`, { uid: true });
+      } finally {
+        lock.release();
+      }
+    } finally {
+      await this.imapClientProvider.closeClient(imapClient);
+    }
+  }
+
  private async compileRawMessage(
    from: string,
    sendMessageInput: SendMessageInput,
@@ -1,4 +1,4 @@
-import { Injectable } from '@nestjs/common';
+import { Injectable, Logger } from '@nestjs/common';

 import { type MessageOutboundDriver } from 'src/modules/messaging/message-outbound-manager/interfaces/message-outbound-driver.interface';

@@ -12,6 +12,8 @@ import { isDefined } from 'twenty-shared/utils';

@Injectable()
 export class MicrosoftMessageOutboundService implements MessageOutboundDriver {
+  private readonly logger = new Logger(MicrosoftMessageOutboundService.name);
+
  constructor(
    private readonly microsoftOAuth2ClientProvider: MicrosoftOAuth2ClientProvider,
  ) {}
@@ -50,6 +52,32 @@ export class MicrosoftMessageOutboundService implements MessageOutboundDriver {
    await this.createDraftMessage(microsoftClient, sendMessageInput);
  }

+  async sendDraft(
+    draftExternalId: string,
+    sendMessageInput: SendMessageInput,
+    connectedAccount: ConnectedAccountEntity,
+  ): Promise<SendMessageResult> {
+    const sendResult = await this.sendMessage(
+      sendMessageInput,
+      connectedAccount,
+    );
+
+    const microsoftClient = await this.microsoftOAuth2ClientProvider.getClient(
+      connectedAccount.id,
+    );
+
+    await microsoftClient
+      .api(`/me/messages/${draftExternalId}`)
+      .delete()
+      .catch((error) =>
+        this.logger.warn(
+          `Failed to delete Microsoft draft ${draftExternalId} after send: ${error}`,
+        ),
+      );
+
+    return sendResult;
+  }
+
  private async createDraftMessage(
    microsoftClient: MicrosoftGraphClient,
    sendMessageInput: SendMessageInput,
@@ -7,4 +7,7 @@ export class SendEmailOutputDTO {

  @Field(() => String, { nullable: true })
  error?: string;
+
+  @Field(() => String, { nullable: true })
+  messageThreadId?: string;
 }
@@ -32,6 +32,9 @@ export class SendEmailInput {
  @Field(() => String, { nullable: true })
  inReplyTo?: string;

+  @Field(() => String, { nullable: true })
+  draftMessageId?: string;
+
  @Field(() => [SendEmailAttachmentInput], { nullable: true })
  files?: SendEmailAttachmentInput[];
 }
@@ -12,4 +12,10 @@ export type MessageOutboundDriver = {
    sendMessageInput: SendMessageInput,
    connectedAccount: ConnectedAccountEntity,
  ): Promise<void>;
+
+  sendDraft(
+    draftExternalId: string,
+    sendMessageInput: SendMessageInput,
+    connectedAccount: ConnectedAccountEntity,
+  ): Promise<SendMessageResult>;
 };
@@ -10,10 +10,12 @@ import { OAuth2ClientManagerModule } from 'src/modules/connected-account/oauth2-
 import { MessagingIMAPDriverModule } from 'src/modules/messaging/message-import-manager/drivers/imap/messaging-imap-driver.module';
 import { MessagingSmtpDriverModule } from 'src/modules/messaging/message-import-manager/drivers/smtp/messaging-smtp-driver.module';
 import { MessagingImportManagerModule } from 'src/modules/messaging/message-import-manager/messaging-import-manager.module';
+import { MessagingMessageCleanerModule } from 'src/modules/messaging/message-cleaner/messaging-message-cleaner.module';
 import { EmailGroupMessageOutboundService } from 'src/modules/messaging/message-outbound-manager/drivers/email-group/services/email-group-message-outbound.service';
 import { GmailMessageOutboundService } from 'src/modules/messaging/message-outbound-manager/drivers/gmail/services/gmail-message-outbound.service';
 import { ImapSmtpMessageOutboundService } from 'src/modules/messaging/message-outbound-manager/drivers/imap/services/imap-smtp-message-outbound.service';
 import { MicrosoftMessageOutboundService } from 'src/modules/messaging/message-outbound-manager/drivers/microsoft/services/microsoft-message-outbound.service';
+import { MessagingDraftSendService } from 'src/modules/messaging/message-outbound-manager/services/messaging-draft-send.service';
 import { MessagingMessageOutboundService } from 'src/modules/messaging/message-outbound-manager/services/messaging-message-outbound.service';
 import { SendEmailService } from 'src/modules/messaging/message-outbound-manager/services/send-email.service';
 import { SentMessagePersistenceService } from 'src/modules/messaging/message-outbound-manager/services/sent-message-persistence.service';
@@ -24,6 +26,7 @@ import { SentMessagePersistenceService } from 'src/modules/messaging/message-out
    MessagingIMAPDriverModule,
    MessagingSmtpDriverModule,
    MessagingImportManagerModule,
+    MessagingMessageCleanerModule,
    EmailingModule,
    TypeOrmModule.forFeature([
      MessageChannelEntity,
@@ -37,12 +40,14 @@ import { SentMessagePersistenceService } from 'src/modules/messaging/message-out
    ImapSmtpMessageOutboundService,
    EmailGroupMessageOutboundService,
    MessagingMessageOutboundService,
+    MessagingDraftSendService,
    SendEmailService,
    SentMessagePersistenceService,
    provideWorkspaceScopedRepository(EmailingDomainEntity),
  ],
  exports: [
    MessagingMessageOutboundService,
+    MessagingDraftSendService,
    SendEmailService,
    SentMessagePersistenceService,
  ],
@@ -23,6 +23,8 @@ import { ConnectedAccountMetadataService } from 'src/engine/metadata-modules/con
 import { SendEmailOutputDTO } from 'src/modules/messaging/message-outbound-manager/dtos/send-email-output.dto';
 import { SendEmailInput } from 'src/modules/messaging/message-outbound-manager/dtos/send-email.input';
 import { SendEmailService } from 'src/modules/messaging/message-outbound-manager/services/send-email.service';
+import { isDefined } from 'twenty-shared/utils';
+import { isNonEmptyString } from '@sniptt/guards';

@MetadataResolver()
@UsePipes(ResolverValidationPipe)
@@ -79,26 +81,60 @@ export class SendEmailResolver {

      const { data } = result;

-      const sendResult = await this.sendEmailService.sendComposedEmail(data);
+      const sendResult = isDefined(input.draftMessageId)
+        ? await this.sendEmailService.sendComposedDraft(
+            data,
+            input.draftMessageId,
+            workspace.id,
+          )
+        : await this.sendEmailService.sendComposedEmail(data);

-      if (data.shouldPersistMessage) {
-        await this.sendEmailService.persistSentMessage(
-          sendResult,
-          data,
-          workspace.id,
+      let messageThreadId: string | undefined;
+
+      try {
+        if (data.shouldPersistMessage) {
+          await this.sendEmailService.persistSentMessage(
+            sendResult,
+            data,
+            workspace.id,
+          );
+        }
+
+        if (isDefined(input.draftMessageId)) {
+          await this.sendEmailService.deleteSentDraft(
+            input.draftMessageId,
+            input.connectedAccountId,
+            workspace.id,
+          );
+        }
+
+        const sentMessageExternalId =
+          sendResult.messageExternalId ?? sendResult.headerMessageId;
+
+        messageThreadId =
+          isDefined(input.draftMessageId) &&
+          isNonEmptyString(sentMessageExternalId)
+            ? await this.sendEmailService.getSentMessageThreadId(
+                sentMessageExternalId,
+                workspace.id,
+              )
+            : undefined;
+
+        const attachmentFileIds = (input.files ?? []).map((file) => file.id);
+
+        if (attachmentFileIds.length > 0) {
+          await this.fileEmailAttachmentService.deleteFiles({
+            fileIds: attachmentFileIds,
+            workspaceId: workspace.id,
+          });
+        }
+      } catch (postSendError) {
+        this.logger.warn(
+          `Email sent but post-send cleanup failed (sync will recover): ${postSendError}`,
        );
      }

-      const attachmentFileIds = (input.files ?? []).map((file) => file.id);
-
-      if (attachmentFileIds.length > 0) {
-        await this.fileEmailAttachmentService.deleteFiles({
-          fileIds: attachmentFileIds,
-          workspaceId: workspace.id,
-        });
-      }
-
-      return { success: true };
+      return { success: true, messageThreadId };
    } catch (error) {
      if (error instanceof ForbiddenException) {
        throw error;
@@ -0,0 +1,171 @@
+import { Injectable } from '@nestjs/common';
+
+import { isNonEmptyString } from '@sniptt/guards';
+import { isDefined } from 'twenty-shared/utils';
+import { In } from 'typeorm';
+
+import { type ConnectedAccountEntity } from 'src/engine/metadata-modules/connected-account/entities/connected-account.entity';
+import { GlobalWorkspaceOrmManager } from 'src/engine/twenty-orm/global-workspace-datasource/global-workspace-orm.manager';
+import { buildSystemAuthContext } from 'src/engine/twenty-orm/utils/build-system-auth-context.util';
+import { type MessageChannelMessageAssociationWorkspaceEntity } from 'src/modules/messaging/common/standard-objects/message-channel-message-association.workspace-entity';
+import { type MessageChannelWorkspaceEntity } from 'src/modules/messaging/common/standard-objects/message-channel.workspace-entity';
+import { MessagingMessageCleanerService } from 'src/modules/messaging/message-cleaner/services/messaging-message-cleaner.service';
+import { MessagingMessageOutboundService } from 'src/modules/messaging/message-outbound-manager/services/messaging-message-outbound.service';
+import { type SendMessageInput } from 'src/modules/messaging/message-outbound-manager/types/send-message-input.type';
+import { type SendMessageResult } from 'src/modules/messaging/message-outbound-manager/types/send-message-result.type';
+
+@Injectable()
+export class MessagingDraftSendService {
+  constructor(
+    private readonly globalWorkspaceOrmManager: GlobalWorkspaceOrmManager,
+    private readonly messageOutboundService: MessagingMessageOutboundService,
+    private readonly messageCleanerService: MessagingMessageCleanerService,
+  ) {}
+
+  async sendDraftMessage({
+    draftMessageId,
+    sendMessageInput,
+    connectedAccount,
+    workspaceId,
+  }: {
+    draftMessageId: string;
+    sendMessageInput: SendMessageInput;
+    connectedAccount: ConnectedAccountEntity;
+    workspaceId: string;
+  }): Promise<SendMessageResult> {
+    const draftAssociation = await this.resolveDraftAssociation(
+      draftMessageId,
+      connectedAccount.id,
+      workspaceId,
+    );
+
+    if (!isDefined(draftAssociation)) {
+      throw new Error(
+        `Could not find a synced draft to send for message ${draftMessageId}`,
+      );
+    }
+
+    return this.messageOutboundService.sendDraft(
+      draftAssociation.messageExternalId,
+      sendMessageInput,
+      connectedAccount,
+    );
+  }
+
+  async getSentMessageThreadId({
+    messageExternalId,
+    workspaceId,
+  }: {
+    messageExternalId: string;
+    workspaceId: string;
+  }): Promise<string | undefined> {
+    const authContext = buildSystemAuthContext(workspaceId);
+
+    return this.globalWorkspaceOrmManager.executeInWorkspaceContext(
+      async () => {
+        const messageChannelMessageAssociationRepository =
+          await this.globalWorkspaceOrmManager.getRepository<MessageChannelMessageAssociationWorkspaceEntity>(
+            workspaceId,
+            'messageChannelMessageAssociation',
+          );
+
+        const association =
+          await messageChannelMessageAssociationRepository.findOne({
+            where: { messageExternalId },
+            relations: ['message'],
+          });
+
+        return association?.message?.messageThreadId ?? undefined;
+      },
+      authContext,
+      { lite: true },
+    );
+  }
+
+  async deleteSentDraft({
+    draftMessageId,
+    connectedAccountId,
+    workspaceId,
+  }: {
+    draftMessageId: string;
+    connectedAccountId: string;
+    workspaceId: string;
+  }): Promise<void> {
+    const draftAssociation = await this.resolveDraftAssociation(
+      draftMessageId,
+      connectedAccountId,
+      workspaceId,
+    );
+
+    if (!isDefined(draftAssociation)) {
+      return;
+    }
+
+    await this.messageCleanerService.deleteMessagesChannelMessageAssociationsAndRelatedOrphans(
+      {
+        workspaceId,
+        messageExternalIds: [draftAssociation.messageExternalId],
+        messageChannelId: draftAssociation.messageChannelId,
+      },
+    );
+  }
+
+  // Scoped to the caller's own channels so a member cannot act on another
+  // member's draft by passing its message id.
+  private async resolveDraftAssociation(
+    draftMessageId: string,
+    connectedAccountId: string,
+    workspaceId: string,
+  ): Promise<{ messageExternalId: string; messageChannelId: string } | null> {
+    const authContext = buildSystemAuthContext(workspaceId);
+
+    const associations =
+      await this.globalWorkspaceOrmManager.executeInWorkspaceContext(
+        async () => {
+          const messageChannelRepository =
+            await this.globalWorkspaceOrmManager.getRepository<MessageChannelWorkspaceEntity>(
+              workspaceId,
+              'messageChannel',
+            );
+
+          const channels = await messageChannelRepository.find({
+            where: { connectedAccountId },
+          });
+
+          const channelIds = channels.map((channel) => channel.id);
+
+          if (channelIds.length === 0) {
+            return [];
+          }
+
+          const messageChannelMessageAssociationRepository =
+            await this.globalWorkspaceOrmManager.getRepository<MessageChannelMessageAssociationWorkspaceEntity>(
+              workspaceId,
+              'messageChannelMessageAssociation',
+            );
+
+          return messageChannelMessageAssociationRepository.find({
+            where: {
+              messageId: draftMessageId,
+              messageChannelId: In(channelIds),
+            },
+          });
+        },
+        authContext,
+        { lite: true },
+      );
+
+    const association = associations.find((currentAssociation) =>
+      isNonEmptyString(currentAssociation.messageExternalId),
+    );
+
+    if (!association || !isNonEmptyString(association.messageExternalId)) {
+      return null;
+    }
+
+    return {
+      messageExternalId: association.messageExternalId,
+      messageChannelId: association.messageChannelId,
+    };
+  }
+}
@@ -93,4 +93,43 @@ export class MessagingMessageOutboundService {
        );
    }
  }
+
+  public async sendDraft(
+    draftExternalId: string,
+    sendMessageInput: SendMessageInput,
+    connectedAccount: ConnectedAccountEntity,
+  ): Promise<SendMessageResult> {
+    switch (connectedAccount.provider) {
+      case ConnectedAccountProvider.GOOGLE:
+        return this.gmailMessageOutboundService.sendDraft(
+          draftExternalId,
+          sendMessageInput,
+          connectedAccount,
+        );
+      case ConnectedAccountProvider.MICROSOFT:
+        return this.microsoftMessageOutboundService.sendDraft(
+          draftExternalId,
+          sendMessageInput,
+          connectedAccount,
+        );
+      case ConnectedAccountProvider.IMAP_SMTP_CALDAV:
+        return this.imapSmtpMessageOutboundService.sendDraft(
+          draftExternalId,
+          sendMessageInput,
+          connectedAccount,
+        );
+      case ConnectedAccountProvider.EMAIL_GROUP:
+      case ConnectedAccountProvider.OIDC:
+      case ConnectedAccountProvider.SAML:
+      case ConnectedAccountProvider.APP:
+        throw new Error(
+          `Provider ${connectedAccount.provider} does not support sending drafts`,
+        );
+      default:
+        assertUnreachable(
+          connectedAccount.provider,
+          `Provider ${connectedAccount.provider} not supported for sending drafts`,
+        );
+    }
+  }
 }
@@ -1,8 +1,10 @@
 import { Injectable, Logger } from '@nestjs/common';

 import { type ComposedEmail } from 'src/engine/core-modules/tool/tools/email-tool/types/composed-email.type';
+import { MessagingDraftSendService } from 'src/modules/messaging/message-outbound-manager/services/messaging-draft-send.service';
 import { MessagingMessageOutboundService } from 'src/modules/messaging/message-outbound-manager/services/messaging-message-outbound.service';
 import { SentMessagePersistenceService } from 'src/modules/messaging/message-outbound-manager/services/sent-message-persistence.service';
+import { type SendMessageInput } from 'src/modules/messaging/message-outbound-manager/types/send-message-input.type';
 import { type SendMessageResult } from 'src/modules/messaging/message-outbound-manager/types/send-message-result.type';

@Injectable()
@@ -11,27 +13,67 @@ export class SendEmailService {

  constructor(
    private readonly messageOutboundService: MessagingMessageOutboundService,
+    private readonly messagingDraftSendService: MessagingDraftSendService,
    private readonly sentMessagePersistenceService: SentMessagePersistenceService,
  ) {}

  async sendComposedEmail(data: ComposedEmail): Promise<SendMessageResult> {
    return this.messageOutboundService.sendMessage(
-      {
-        to: data.recipients.to,
-        cc: data.recipients.cc.length > 0 ? data.recipients.cc : undefined,
-        bcc: data.recipients.bcc.length > 0 ? data.recipients.bcc : undefined,
-        subject: data.sanitizedSubject,
-        body: data.plainTextBody,
-        html: data.sanitizedHtmlBody,
-        attachments: data.attachments,
-        inReplyTo: data.inReplyTo,
-        threadExternalId: data.threadExternalId,
-        references: data.references,
-      },
+      this.toSendMessageInput(data),
      data.connectedAccount,
    );
  }

+  async sendComposedDraft(
+    data: ComposedEmail,
+    draftMessageId: string,
+    workspaceId: string,
+  ): Promise<SendMessageResult> {
+    return this.messagingDraftSendService.sendDraftMessage({
+      draftMessageId,
+      sendMessageInput: this.toSendMessageInput(data),
+      connectedAccount: data.connectedAccount,
+      workspaceId,
+    });
+  }
+
+  async deleteSentDraft(
+    draftMessageId: string,
+    connectedAccountId: string,
+    workspaceId: string,
+  ): Promise<void> {
+    await this.messagingDraftSendService.deleteSentDraft({
+      draftMessageId,
+      connectedAccountId,
+      workspaceId,
+    });
+  }
+
+  async getSentMessageThreadId(
+    messageExternalId: string,
+    workspaceId: string,
+  ): Promise<string | undefined> {
+    return this.messagingDraftSendService.getSentMessageThreadId({
+      messageExternalId,
+      workspaceId,
+    });
+  }
+
+  private toSendMessageInput(data: ComposedEmail): SendMessageInput {
+    return {
+      to: data.recipients.to,
+      cc: data.recipients.cc.length > 0 ? data.recipients.cc : undefined,
+      bcc: data.recipients.bcc.length > 0 ? data.recipients.bcc : undefined,
+      subject: data.sanitizedSubject,
+      body: data.plainTextBody,
+      html: data.sanitizedHtmlBody,
+      attachments: data.attachments,
+      inReplyTo: data.inReplyTo,
+      threadExternalId: data.threadExternalId,
+      references: data.references,
+    };
+  }
+
  async persistSentMessage(
    sendResult: SendMessageResult,
    data: ComposedEmail,
@@ -55,5 +55,6 @@ export const formatSentMessage = (
    direction: MessageDirection.OUTGOING,
    attachments: [],
    participants,
+    isDraft: false,
  };
 };