Why does mail sync with Outlook not work?

I am using Mail on my MacBook Air (2020) running Catalina to access my emails from an enterprise MS Outlook server. Unfortunately, there are major hiccups - in particular, the operations I do locally on my Mac are not reflected in the Outlook mailboxes (which I can see in a Web-based interface), and, even worse, Outlook mail doesn't always get copied to my Inbox on Mail.

Part of the problem is a persistent message (bottom left corner of the Message Viewer as well as the Activity Viewer) that says "Moving Messages 1 of 30" - for HOURS on end, with no change (and no actual messages being moved). I tried the "Synchronize" menu item, as well as "Rebuilt", "Get New Mail", and taking the account offline and back online. This only resulted in ALL emails in that Inbox disappearing entirely! Quitting and reopening Mail and even restarting the computer doesn't do ANYTHING. It's NOT a connection issue - the Connection Doctor shows everything is fine (green).


Meanwhile, new emails are showing up again, and my Google Account works normally and is nicely synched. But those emails that are still clearly in my Outlook Inbox simply do not reappear in my Mail Inbox. Even stranger, there is no problem with my OTHER Mac (MacBook Pro 2018 running Mojave) which is completely synched with my Outlook accounts - only the Air with Catalina shows this problem.


Any ideas?

MacBook Air 13", macOS 10.15

Posted on May 12, 2020 10:10 AM

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9 replies

May 13, 2020 2:12 PM in response to Sebastian Kuhn

Hello again Sebastian Kuhn,


Thanks again for your prompt reply.


We can not guarantee anything, but if rebuilding, "getting new mail", and taking your account offline and online again does not work, then the next steps would be to completely remove the account from the device. This will help to re-establish a connection with your email server.


Any emails stored "On My Mac" will remain on your computer. Any emails stored through Exchange/Outlook servers will come back upon signing back into your email account.


You can perform a backup of your Mac just to make sure everything that is locally stored on the Mac is backed up.


Back up your Mac


Let us know if you have any questions or need further assistance.


Best regards!

May 15, 2020 7:42 AM in response to Teddy_B

I followed your advice, completely removed the Exchange account from my MacBook Air, and then added it again in Mail.

The good news: It worked without problems, and my Inbox now is complete again. Strangely, while I had to agree that the Exchange account would be removed from ALL my Macs, when I restarted my MacBook Pro (which was shut down during this operation), everything was in place as before - no need to re-add the account there. Fine by me, but somewhat disconcerting if things don't behave as expected.

The bad news: While the Inbox has been fully restored, one of the other mailboxes of that account has disappeared entirely (the first out of 39), without any rhyme nor reason. Everything else seems to be in place, but this is decidedly odd. (I found a workaround, but only by moving the content of that mailbox on my MacBook Pro, where it was untouched, to a different mailbox).

In summary - it seems I'm o.k. for now, but I continue to be concerned by odd behavior. I would suggest that Mail in Catalina needs a bug-fix upgrade!

May 13, 2020 12:09 PM in response to Teddy_B

Thank you for helping me with this - much appreciated. First off, I re-checked and, yes, my software is fully up-to-date. I then followed your advice to set up a new user (I had to laugh when I followed your link as the page was in Korean or some other script unknown to me, but I know anyway how to do this). I set up Mail with my MS Exchange account (sorry, of course it's EXCHANGE, not "Outlook" as I incorrectly wrote earlier), and lo and behold, everything showed up as it should. I did a couple tests - it appears (so far) as if Mail for this new user does indeed synchronize this account nicely with whatever I do on my other Mac.

On point that may be relevant is that I did NOT enable my AppleID when I set up that new account. My standard account does have Apple ID enabled, and when I tried to remove the Exchange account to see if I can set it up from scratch, I was only given the option to "disable" it on my MacBook Air or delete it simultaneously on ALL my devices (including iPhone). Of course I didn't dare choose the latter, so I chose "disable" which simply made the account greyed-out in the Internet Accounts listing in System Preferences, but not disappear. When I then tried to "add account" in Mail, it would recognize that the account already existed and only gave me the option to re-enable Mail, Contacts etc.. I did that, and ALL of the previously visible mailboxes appeared again, with the EXACT same content (including with everything from before yesterday still missing from my Inbox, while it's still there on all other devices, in Outlook and in my new user account on the MacBook Air). So I am wondering whether there is some conflict between AppleID/iCloud and setting up an account cleanly.

May 13, 2020 12:52 PM in response to i_rina

This sounds really scary. This is my main work email - right now it works just fine on my MacBook Pro, my iPhone, and on the "other user" on my MacBook Air. Can you guarantee that by removing it from ALL of these devices, I won't end up loosing a bunch of older emails from my Inbox as happened on my main account on the MacBook Air? (For what it's worth, it is still eternally spinning "Moving Messages 1 of 22"...)

Not to mention the work required to set it up again everywhere...

May 19, 2020 10:49 AM in response to Teddy_B

Here is an update on my Mail issues: While it worked for a while, Mail on my MacBook Air (running Catalina) and my MacBook Pro (running Mojave) have once again fallen out of sync. In particular, any action I perform on one of my Exchange mails on my Air (e.g., delete) is not reflected on the actual Exchange account or the MacBook Pro. And once again, the persistent message pops up on my Air in the bottom left corner of Mail, saying "Moving Messages 1 of 10" forever without a change. So much to my regret, I'm pretty much back to where I was when I sent out my initial request for help. Can anybody tell me what else I could try? What is the Mac actually DOING while it incessantly displays this "Moving..." message?

May 13, 2020 8:23 AM in response to Sebastian Kuhn

Hello Sebastian Kuhn,


Thanks for using the Apple Support Communities! I understand that Outlook on your Mac does not sync what you are doing from your current device to others. I can definitely see how this could be concerning. I'm happy to help!


Let's first make sure the Mac is fully up-to-date.

How to update the software on your Mac


We will also try to test this behavior in a new user to see if this continues to happen. Please follow this resource to create a user on your Mac. Please then login to this new user and open the Mail application to add your Outlook account. Test to see if this behavior continues.

Set up users, guests, and groups on Mac


Please respond back if you continue to have any issues.


Cheers!

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Why does mail sync with Outlook not work?

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