Integrate IMAP and SMTP clients for message sending #14688

JealousGx · 2025-09-24T13:02:33Z

Implement functionality to send messages using both IMAP and SMTP clients, allowing for message storage in the Sent folder.

Closes #14379

github-actions · 2025-09-24T13:03:26Z

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greptile-apps

Greptile Overview

Summary

This PR implements IMAP and SMTP client integration for message sending, addressing the feature request to copy workflow-sent emails to the "Sent" folder. The implementation adds support for storing sent messages in IMAP accounts' Sent folders.

Key Changes:

Added IMAP client integration alongside SMTP for IMAP_SMTP_CALDAV provider
Implemented parallel client initialization and proper message composition using MailComposer
Added automatic copying of sent messages to the Sent folder when available
Simplified Gmail message composition by removing multipart/alternative format
Removed HTML support from the interface, now only supporting plain text messages

Critical Issues Found:

Resource leak: SMTP client connections are not properly closed
Removed HTML support breaks backward compatibility for existing workflows
Missing error handling for IMAP operations could lead to partial failures
Potential inconsistency between message formats across different providers

Confidence Score: 2/5

This PR has critical resource management and backward compatibility issues
Score reflects resource leaks, breaking changes to HTML support, insufficient error handling for IMAP operations, and potential partial failure scenarios
messaging-send-message.service.ts requires attention for resource management, error handling, and backward compatibility

Important Files Changed

File Analysis

Filename	Score	Overview
packages/twenty-server/src/modules/messaging/message-import-manager/services/messaging-send-message.service.ts	2/5	integrates IMAP/SMTP for message sending with Sent folder storage, but removes HTML support and has resource leak issues

Sequence Diagram

sequenceDiagram
    participant W as Workflow
    participant MS as MessagingSendMessageService
    participant SC as SmtpClient
    participant IC as ImapClient
    participant GC as GmailClient
    participant MC as MicrosoftClient
    participant SF as SentFolder

    W->>MS: sendMessage(input, connectedAccount)
    
    alt Google Provider
        MS->>GC: getGmailClient()
        MS->>GC: userinfo.get()
        MS->>MS: buildHeaders(fromEmail, fromName)
        MS->>GC: users.messages.send(encodedMessage)
    else Microsoft Provider
        MS->>MC: getMicrosoftClient()
        MS->>MC: api('/me/messages').post(message)
        MS->>MC: api('/me/messages/{id}/send').post()
    else IMAP_SMTP_CALDAV Provider
        par Parallel Client Setup
            MS->>SC: getSmtpClient()
        and
            MS->>IC: getClient()
        end
        MS->>MS: new MailComposer(messageData)
        MS->>MS: compile().build() -> messageBuffer
        MS->>SC: sendMail(rawMessage)
        MS->>IC: list() -> folders
        MS->>SF: find(specialUse === '\\Sent')
        alt Sent Folder Found
            MS->>IC: append(sentFolder.path, messageBuffer)
        end
        MS->>IC: closeClient()
        Note over MS,SC: SMTP client not closed (resource leak)
    end

_{1 file reviewed, 4 comments}

_{Edit Code Review Bot Settings | Greptile}

greptile-apps · 2025-09-24T13:06:53Z

...rver/src/modules/messaging/message-import-manager/services/messaging-send-message.service.ts

+          to: [sendMessageInput.to],
+          raw: messageBuffer,
+        });


style: use object destructuring for better readability

Suggested change

to: [sendMessageInput.to],

raw: messageBuffer,

});

await smtpClient.sendMail({

from: connectedAccount.handle,

to: [sendMessageInput.to],

raw: messageBuffer,

});

@JealousGx
Could you please address this last comment?

greptile-apps · 2025-09-24T13:06:54Z

...rver/src/modules/messaging/message-import-manager/services/messaging-send-message.service.ts

+        const sentFolder = await imapClient
+          .list()
+          .then((folders) =>
+            folders.find((folder) => folder.specialUse === '\\Sent'),
+          );
+
+        if (isDefined(sentFolder)) {
+          await imapClient.append(sentFolder.path, messageBuffer);
+        }


logic: if the Sent folder lookup fails (network error, permissions), the message is sent but not saved to Sent folder. add error handling to ensure message is either fully sent and saved, or operation fails completely

Suggested change

const sentFolder = await imapClient

.list()

.then((folders) =>

folders.find((folder) => folder.specialUse === '\\Sent'),

);

if (isDefined(sentFolder)) {

await imapClient.append(sentFolder.path, messageBuffer);

}

const sentFolder = await imapClient

.list()

.then((folders) =>

folders.find((folder) => folder.specialUse === '\\Sent'),

)

.catch((error) => {

throw new MessageImportDriverException(

`Failed to find Sent folder: ${error.message}`,

MessageImportDriverExceptionCode.CLIENT_NOT_AVAILABLE,

);

});

if (isDefined(sentFolder)) {

await imapClient.append(sentFolder.path, messageBuffer)

.catch((error) => {

throw new MessageImportDriverException(

`Failed to save message to Sent folder: ${error.message}`,

MessageImportDriverExceptionCode.CLIENT_NOT_AVAILABLE,

);

});

}

greptile-apps · 2025-09-24T13:06:54Z

...rver/src/modules/messaging/message-import-manager/services/messaging-send-message.service.ts

+          await imapClient.append(sentFolder.path, messageBuffer);
+        }
+
+        await this.imapClientProvider.closeClient(imapClient);


logic: IMAP client is closed but SMTP client is not. this creates resource leaks for SMTP connections

github-actions · 2025-09-24T13:14:16Z

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neo773 · 2025-09-24T14:03:01Z

...rver/src/modules/messaging/message-import-manager/services/messaging-send-message.service.ts

+          raw: messageBuffer,
+        });
+
+        const sentFolder = await imapClient


This is not efficient and also doesn't accounts for edge cases that ImapFindSentFolderService handles

I would suggest you to get the sent folder from messageFolders table instead, filter by isSentFolder: true

Actually no need to query anything, connectedAccount already has messageChannel and messageFolders

you can do something like

const messageChannel = connectedAccount.messageChannels.find( (channel) => channel.handle === connectedAccount.handle ); const sentFolder = messageChannel?.messageFolders.find( (messageFolder) => messageFolder.isSentFolder );

neo773 · 2025-09-24T14:16:25Z

...rver/src/modules/messaging/message-import-manager/services/messaging-send-message.service.ts

-          await this.smtpClientProvider.getSmtpClient(connectedAccount);
+        const [smtpClient, imapClient] = await Promise.all([
+          this.smtpClientProvider.getSmtpClient(connectedAccount),
+          this.imapClientProvider.getClient(connectedAccount),


imapClientProvider.getClient() will throw an error if the user doesn't have an IMAP account connected, this assumes user will always have one.

I don't think there's much we can do on the backend in that case. For convenience, I've added logs when we can't get IMAP account.

…nding failures

neo773 · 2025-09-25T10:11:25Z

...rver/src/modules/messaging/message-import-manager/services/messaging-send-message.service.ts

-          .list()
-          .then((folders) =>
-            folders.find((folder) => folder.specialUse === '\\Sent'),
+        try {


Remove this and call the client conditionally

isDefined(connectedAccount.connectionParameters?.IMAP)

…ge method

…er code

neo773 · 2025-09-26T09:34:57Z

@JealousGx
Hi, could you please fix the failing tests in CI?

feat(messaging): integrate IMAP and SMTP clients for sending messages

f3a093f

greptile-apps bot reviewed Sep 24, 2025

View reviewed changes

neo773 suggested changes Sep 25, 2025

View reviewed changes

feat(messaging): enhance IMAP handling and add logging for message se…

869a5e3

…nding failures

neo773 reviewed Sep 25, 2025

View reviewed changes

JealousGx added 4 commits September 25, 2025 15:17

refactor(messaging): remove logger and streamline IMAP message handling

11e2a14

refactor(messaging): simplify connected account handling in sendMessa…

2bf4b2e

…ge method

Merge branch 'main' into feat/emails-sent

b98768b

Refactor sendMessage method to destructure sendMessageInput for clean…

0a8d324

…er code

JealousGx requested a review from neo773 September 26, 2025 07:39

JealousGx added 2 commits September 26, 2025 17:36

Add ImapClientProvider to MessagingSendMessageService test setup

3fbbbbc

Merge branch 'main' into feat/emails-sent

ac99c25

FelixMalfait assigned neo773 Oct 2, 2025

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Integrate IMAP and SMTP clients for message sending #14688

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neo773 commented Sep 26, 2025

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Integrate IMAP and SMTP clients for message sending #14688

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Integrate IMAP and SMTP clients for message sending #14688

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Greptile Overview

Summary

Confidence Score: 2/5

Important Files Changed

Sequence Diagram

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