Outlook for MAC is not syncing sent folder for IMAP account

Anonymous
2022-02-23T01:00:04+00:00

Hello,

Has anyone seen an issue where the outlook app on MacBook pro is not syncing sent messages in the local sent folder with the sent folder on the email server? This issue is for a domain and email hosted through a 3rd party hosting provider. The outlook app uses IMAP settings to connect to the email account.

The emails, however, are being sent to the destination, and it is just that a copy stored in the sent folder of the outlook app is not syncing with that of the email server through IMAP.

I would appreciate any ideas on how to fix this. Many thanks for considering my request.

Outlook | MacOS | Legacy Outlook for Mac | For business

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  1. Anonymous
    2023-03-15T08:59:26+00:00

    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?

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  2. Anonymous
    2023-02-13T10:43:28+00:00

    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.

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  3. Anonymous
    2023-02-10T21:16:44+00:00

    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.

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  4. Anonymous
    2023-02-07T13:12:23+00:00

    UGH, @Tim Sharpe!!! That sounds horrible. Well, I have stopped trying to use Outlook, which is very sad, but I have a workable system using webmail. Because my email account is not a Microsoft account, it won't let me click to add an email to Onenote, but I have learned to just take screen shots of the email and paste it into my Onenote. That is working so well, and I am back on track with my way of organizing certain emails that I am abandoning any attempt to go back to Outlook.

    I like my Macbook. As a lifelong PC user, this has been an easier switch than I thought. (I just wish there was a built in paint program like Windows Paint 3D; that was amazing!) I also like my Microsoft 365 home subscription and will likely die before I cancel it. I wish my Mac worked better with 365, but I'm good right now.

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  5. Anonymous
    2023-02-07T08:51:55+00:00

    Hi. I've had this exact same issue. I do have a fix of sorts. Deleting and reinstalling the iCloud account does work BUT!! this then deletes all the sent messages in the SENT folder on Outlook which haven't synced. I found this to my cost. The fix described previous on this thread, to set up a new iCloud account, but not using microsoft sync services does seem to address the issue, but noting my previous comment, if this is a replacement account you may lose sent emails in Outlook.

    My fix is to set up a second iCloud account using the alternative iCloud address, and don't use sync services. Outlook won't let you set up a duplicate with the same email address, but the alternative XXX@icloud ******@mac.com or ******@me.com seems to work.

    UPDATE... Meh. It looks like the new account (not using microsoft sync) doesn't allow search facility - its might be that its re-indexing but at present I can't search for emails in the 'new' account.

    UPDATE 2 .. OK it worked for a while, but then sync failed again, so back to square 1.

    Would be nice to have a proper fix for this...

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