Outlook For Mac - Sent Folder Does Not Sync

Question

Hello,

I have been using Apple Mail on all Mac computers (and iOS devices) to date but would like to use Outlook on my office MacBook and Apple Mail on different devices (using the same email account @iCloud.com).

I installed Outlook (16.40) on my 2020 MacBook OSX 10.15.6 and set up the account information (IMAP) and started synchronizing the folders.

As far as I can tell, all of the folders have populated on the MacBook but the sent folder does not synchronize. Further, when I send an email in Outlook (@iCloud.com) from the MacBook, the email will show in the sent folder on that computer but not on any other device.

I am not using Exchange Server. 

Is there a way to have the sent folder synchronize with my iCloud mail account so all sent items on this macBook appear in the sent folders of all of my other devices whether in Apple's Mail program or Outlook for Mac?

Thank you.

jhk

Answer 1

Hello Jhk, 

Is there any updates about this issue?

Regards,

Jennifer

Answer 2

Hello Jhk,

To troubleshoot your problem, please firstly make sure you have correctly configured your iCloud account as described in this article: Microsoft Outlook for Mac compatibility with Apple iCloud.

Meanwhile, please go to the View menu and click IMAP folders, then try to un-subscribe and re-subcribe to the Sent items folder your IMAP to see if this can help to fix this issue. If it doesn't help, you can back up your data, then remove and re-add your account to see if this will make any difference.

Besides, please kindly do below tests to further narrow down this issue:

1. Send a test email from Outlook for Mac and login to your iCloud account via the web browser to see if you can see the test email in the Sent items folder.
2. Send a test email 2 from the iCloud online and check if the test email 2 can be synced to the Sent items folder in Outlook for Mac.

Best regards,

Jennifer 

Hi Jennifer,

This Outlook mailbox was set up as new yesterday. On a Mac, I don't have an option to go to "View" "IMAP folders". On the Mac top bar (to the right of the small apple icon, I can select "Tools" "IMAP Folders" and I can browse all of the folders but all of the action buttons at the top of that pane (subscribe/unsubscribe) and greyed out.

1. Sending from Outlook for Mac and logging into iCloud mail to view the sent folder, the item is not showing in the web based iCloud Mail "sent" folder.
2. Sending test email from iCloud online, test email shows in iCloud and iOS devices in Apple Mail's sent folder, but does not appear in Outlook for Mac sent folder.

Thoughts? I'm afraid without the sent folder syncing across all iOS, OSX devices, Outlook mail is not usable for me.

Thanks,

jhk

Answer 3

Hello Jhk,

Thanks for your reply. Based on this article, it is supported to sync emails for IMAP account in Outlook.

However, from your description, it seems Outlook for Mac fails to sync emails from the iCloud email server. May I confirm if you can receive the test emails that send from Outlook for Mac?  

If no, please go to Tools > Accounts, select your account to double check if your IMAP account configuration is the same as described in this article: Microsoft Outlook for Mac compatibility with Apple iCloud.

Also, try updating your Outlook for Mac client to the latest version 16.41 and check if this will make any difference.

To help you further, may I confirm if there is any error messages in Tools > Sync Errors? If so, please send us a screenshoot of the error message for analysis.

Best regards,

Jennifer

Answer 4

Hello Jhk,

To troubleshoot your problem, please firstly make sure you have correctly configured your iCloud account as described in this article: Microsoft Outlook for Mac compatibility with Apple iCloud.

Meanwhile, please go to the View menu and click IMAP folders, then try to un-subscribe and re-subcribe to the Sent items folder your IMAP to see if this can help to fix this issue. If it doesn't help, you can back up your data, then remove and re-add your account to see if this will make any difference.

Besides, please kindly do below tests to further narrow down this issue:

1. Send a test email from Outlook for Mac and login to your iCloud account via the web browser to see if you can see the test email in the Sent items folder.
2. Send a test email 2 from the iCloud online and check if the test email 2 can be synced to the Sent items folder in Outlook for Mac.

Best regards,

Jennifer