Outlook for MAC is not syncing sent folder for IMAP account

Hello,

Just to summarize the significance of the issue with iCloud accounts configured in Outlook using "Sync with Microsoft Cloud" (vs. IMAP)...

• You will permanently lose every message sent from this account if you remove the account from Outlook.
• You will never be able to restore those sent messages from a local backup (viaTime Machine, Backblaze, etc.) as those messages aren't truly stored on your local computer, so they aren't being backed up.
• It's highly unlikely Microsoft will restore those messages from their server as they informed me they aren't backed up. (FWIW, I don't believe that's true, but Microsoft support never wavered on this statement.)

So, to put it bluntly, if your iCloud account is configured in Outlook using "Sync with Microsoft Cloud", your sent messages are NOT being backed up in any way shape or form. If you make the mistake of removing it from Outlook, they are gone. Forever.

That being said, here's one thing you can do. You can drag those sent messages to a Finder folder. This will allow them to be backed up (since they are now stored on your local computer) and opened by Outlook or another mail client. Mind you, it appears Outlook can only handle dragging/dropping 75 messages at a time, so it's going to take a little time. FYI: When you open a message from Finder into Outlook, Outlook gives you the option of importing the message into an Outlook folder of your choosing. However, that import hasn't worked for me.

Separately, you should be able to create an additional iCloud email account in Outlook, using the same iCloud email address, but configured using IMAP. This is now my go-to iCloud email account, but I still have the old "sync with Microsoft cloud" account setup for historical sent messages.

In my experience, setting up an IMAP returns the same issues - emails sent via Outlook do not sync with the iCloud sent message folder and as Chewbach reports above, deleting and reinstalling an iCloud account will lead to ALL messages being sent via Outlook being deleted.

And as reported, a time machine backup will not fix this.

I am now reverting to the use of Apple Mail for iCloud emails, this bug is too serious to rely on Outlook.

I see my sent items in the New Outlook but not the Legacy Outlook. Is there a way to move it out from the New Outlook sent folder to the Legacy outlook sent folder?

The only thing I was able to do was drag them into a Finder folder, then import them into the Apple's mail.app. Oddly enough, those sent items are now visible to everything except new Outlook.

how do you import them exactly and will the be put into the right folder directly with the correct date or how does this work properly?