diff --git a/packages/twenty-server/src/engine/core-modules/tool/tools/send-email-tool/send-email-tool.ts b/packages/twenty-server/src/engine/core-modules/tool/tools/send-email-tool/send-email-tool.ts
index 3aa0554ca9126..9733019edefb0 100644
--- a/packages/twenty-server/src/engine/core-modules/tool/tools/send-email-tool/send-email-tool.ts
+++ b/packages/twenty-server/src/engine/core-modules/tool/tools/send-email-tool/send-email-tool.ts
@@ -50,8 +50,14 @@ export class SendEmailTool implements Tool {
         workspaceId,
         'connectedAccount',
       );
-    const connectedAccount = await connectedAccountRepository.findOneBy({
-      id: connectedAccountId,
+
+    const connectedAccount = await connectedAccountRepository.findOne({
+      where: { id: connectedAccountId },
+      relations: {
+        messageChannels: {
+          messageFolders: true,
+        },
+      },
     });
 
     if (!isDefined(connectedAccount)) {
diff --git a/packages/twenty-server/src/modules/messaging/message-import-manager/services/__tests__/messaging-send-message-gmail.spec.ts b/packages/twenty-server/src/modules/messaging/message-import-manager/services/__tests__/messaging-send-message-gmail.spec.ts
index 2aef95c90ff74..f0bd62e8fad18 100644
--- a/packages/twenty-server/src/modules/messaging/message-import-manager/services/__tests__/messaging-send-message-gmail.spec.ts
+++ b/packages/twenty-server/src/modules/messaging/message-import-manager/services/__tests__/messaging-send-message-gmail.spec.ts
@@ -4,6 +4,7 @@ import { ConnectedAccountProvider } from 'twenty-shared/types';
 
 import { GmailClientProvider } from 'src/modules/messaging/message-import-manager/drivers/gmail/providers/gmail-client.provider';
 import { OAuth2ClientProvider } from 'src/modules/messaging/message-import-manager/drivers/gmail/providers/oauth2-client.provider';
+import { ImapClientProvider } from 'src/modules/messaging/message-import-manager/drivers/imap/providers/imap-client.provider';
 import { MicrosoftClientProvider } from 'src/modules/messaging/message-import-manager/drivers/microsoft/providers/microsoft-client.provider';
 import { SmtpClientProvider } from 'src/modules/messaging/message-import-manager/drivers/smtp/providers/smtp-client.provider';
 import { MessagingSendMessageService } from 'src/modules/messaging/message-import-manager/services/messaging-send-message.service';
@@ -53,6 +54,10 @@ describe('MessagingSendMessageService - Gmail HTML Support', () => {
           provide: SmtpClientProvider,
           useValue: {},
         },
+        {
+          provide: ImapClientProvider,
+          useValue: {},
+        },
       ],
     }).compile();
 
diff --git a/packages/twenty-server/src/modules/messaging/message-import-manager/services/messaging-send-message.service.ts b/packages/twenty-server/src/modules/messaging/message-import-manager/services/messaging-send-message.service.ts
index 58c5026a6f13b..7c50aeb6ec423 100644
--- a/packages/twenty-server/src/modules/messaging/message-import-manager/services/messaging-send-message.service.ts
+++ b/packages/twenty-server/src/modules/messaging/message-import-manager/services/messaging-send-message.service.ts
@@ -1,5 +1,6 @@
 import { Injectable } from '@nestjs/common';
 
+import MailComposer from 'nodemailer/lib/mail-composer';
 import { ConnectedAccountProvider } from 'twenty-shared/types';
 import { assertUnreachable, isDefined } from 'twenty-shared/utils';
 import { z } from 'zod';
@@ -11,6 +12,7 @@ import {
 } from 'src/modules/messaging/message-import-manager/drivers/exceptions/message-import-driver.exception';
 import { GmailClientProvider } from 'src/modules/messaging/message-import-manager/drivers/gmail/providers/gmail-client.provider';
 import { OAuth2ClientProvider } from 'src/modules/messaging/message-import-manager/drivers/gmail/providers/oauth2-client.provider';
+import { ImapClientProvider } from 'src/modules/messaging/message-import-manager/drivers/imap/providers/imap-client.provider';
 import { MicrosoftClientProvider } from 'src/modules/messaging/message-import-manager/drivers/microsoft/providers/microsoft-client.provider';
 import { isAccessTokenRefreshingError } from 'src/modules/messaging/message-import-manager/drivers/microsoft/utils/is-access-token-refreshing-error.utils';
 import { SmtpClientProvider } from 'src/modules/messaging/message-import-manager/drivers/smtp/providers/smtp-client.provider';
@@ -30,6 +32,7 @@ export class MessagingSendMessageService {
     private readonly oAuth2ClientProvider: OAuth2ClientProvider,
     private readonly microsoftClientProvider: MicrosoftClientProvider,
     private readonly smtpClientProvider: SmtpClientProvider,
+    private readonly imapClientProvider: ImapClientProvider,
   ) {}
 
   public async sendMessage(
@@ -134,16 +137,47 @@ export class MessagingSendMessageService {
         break;
       }
       case ConnectedAccountProvider.IMAP_SMTP_CALDAV: {
+        const { handle, connectionParameters, messageChannels } =
+          connectedAccount;
+
         const smtpClient =
           await this.smtpClientProvider.getSmtpClient(connectedAccount);
 
-        await smtpClient.sendMail({
-          from: connectedAccount.handle,
+        const mail = new MailComposer({
+          from: handle,
           to: sendMessageInput.to,
           subject: sendMessageInput.subject,
           text: sendMessageInput.body,
           html: sendMessageInput.html,
         });
+
+        const messageBuffer = await mail.compile().build();
+
+        await smtpClient.sendMail({
+          from: handle,
+          to: sendMessageInput.to,
+          raw: messageBuffer,
+        });
+
+        if (isDefined(connectionParameters?.IMAP)) {
+          const imapClient =
+            await this.imapClientProvider.getClient(connectedAccount);
+
+          const messageChannel = messageChannels.find(
+            (channel) => channel.handle === handle,
+          );
+
+          const sentFolder = messageChannel?.messageFolders.find(
+            (messageFolder) => messageFolder.isSentFolder,
+          );
+
+          if (isDefined(sentFolder)) {
+            await imapClient.append(sentFolder.name, messageBuffer);
+          }
+
+          await this.imapClientProvider.closeClient(imapClient);
+        }
+
         break;
       }
       default: