Mail issue with MS exchange server on macOS Catalina

I have exactly the same issue, since updating to Catalina on my MacBookPro. AppleMail e failing to correctly synchronise with my Exchange Server - if I open MSFT Outlook on that same computer, it does not show any sent emails, and the read/unread status in not up-to-date - same goes with my iPhone (iOS12) and iPad(iPadOS13)... I hope this is fixed ASAP!

Strangely enough, things seem to be fixed now, without any intervention (as far as I can realize) from my side... AppleMail on 10.15.1seems to be syncing all sent messages with the MSFT Exchange server, and all is right between my iPhone, iPad, AppleMail and Outlook clients... weird, but at least the problem seems to have been fixed somehow...

I have the very same problem on my new macbook pro (Catalina 10.15.2: no changes made on my exchange account via the mail app on my computer are synced on my iOS devices or on the exchange server. The problem exists since several weeks now. Hope this can be solved by a macOS update soon.

Thanks for the hints. I did not have more than 5.000 messages, at least if the calender entries are not considered.

In the linked support document I have seen the hint to disable the automatic connection settings. Wait and see, if this works.

Interesting wise with iOS everything is running perfekt.

This is exactly the issue I have with mail, since upgrading to Catalina. No communication whatsoever between Microsoft Exchange and OS X.. If I remove mails from my inbox to a local folder, my exchange does not get updated, and if I read emails, this is not updated either. Quite annoying, and I suspect apple won't care since it is tied to Microsoft. What a disgrace.

Dutchdontdance wrote:

This is exactly the issue I have with mail, since upgrading to Catalina. No communication whatsoever between Microsoft Exchange and OS X.. If I remove mails from my inbox to a local folder, my exchange does not get updated, and if I read emails, this is not updated either. Quite annoying, and I suspect apple won't care since it is tied to Microsoft. What a disgrace.

Microsoft has had ongoing issues with Exchange and ActiveSync for quite a while.

cf. https://support.microsoft.com/en-us/help/2563324/current-issues-with-exchange-activesync-and-third-party-device

I can tell you that Office 365--while functional--is nothing short of glacially slow when it comes to downloading/syncing e-mail.

I recently purchased an iMac 27" and am currently running Catalina 10.15.2.

I had a 21.5" 2011iMac that I backed up to Time Machine and used the Time Machine backup to load onto my new iMac.

My Gmail and normal Mail accounts are working just fine but the Exchange account isn't updating to what is shown on my iPhone, MacBook Air, or office PC that I use.

Is there some kind of bug that hasn't been worked out between Exchange server and Catalina?

This wasn't a problem on High Sierra that I was using on the 21.5 inch iMac.

10.15.3 bring no improvement in Apple Mail? ****.

I also have this other strange problem: when scrolling through my Exchange email (in the Apple Mail client), subsequent messages from different people but on the same subject do not display the new content. So, if I read person A's email on subject x, down a few messages, if I come across another mail message from person B on the same subject, it will actually display the mail from person A. I have to leave it and come at the message from a different direction or double click on it to see it, specifically. Annoying!

Anyways, Apple, if you are listening, Mail needs to be fixed.

I have the very same problem. I use three iMacs in three different cities and a Macbook with thousands of emails in hundreds of folders and they synced perfectly well in the past, but since a few weeks ago it all has gone into a nightmare, I have to file the same emails four times, one in each computer, as they won't sync. Thank good the problem didn't extend to Archives app, but if Apple loses its reliability with this email sync matter its a bad thing ...! Hope this will be fixed asap!

Best,

This suggestion is not new; others have tried it, including me, but the anomalies and problems eventually return. But, 10.15.3 may fix it. We will see if it stays fixed.

Regardless, thank you for engaging in this discussion. 🙂

It seems to me that Apple is less serious about serious "professional" use of their products. Mail is so intrinsic to many things; there's no excuse for not fixing these problems, let alone, having distributed it in the first place.

Same problem "moving mails". I have reinstalled the Exchange account and nothing happened. The main problem appears when I want to move my read e-mails to separate folders that I have created in "On my Mac". The messages never move or if they move they are empty or blank. Another issue that I found is that when I erase a message from the app mail of my MacBook Pro, such message does not delete from my iPad and iPhone. I don't know what to do.

Any feedback on the VPN client being part of the problem. I have documented this issue as well as sent feedback to apple, I did not get an acknowledgement , what ****** me, is it in an old problem. apple can point its fingers on Microsoft and microsoft can simply say - outlook mail but how about the loyalist of apple mail? just fix it!

I usually do not have any VPN running. Occasionally, I do (Cisco's). I can see no correlation to a VPN. Furthermore, I have backup systems that do not have any VPN software installed but still see this problem. Finally, my Apple Calendar syncs just fine with the Exchange Calendar. Again, the Apple Mail client can receive and send Exchange mail messages just fine. As an aside, I have tested it with firewall off (all ports open). The problems (as I've previously described) still persist.

Today essentially begins day 3 and the first business day. Things are continuing to work nicely.

@Lauener: I agree that this "fix" *****. But, at this point, I have exhausted all else. So, I bit the bullet. I further agree to being REALLY unhappy with not finding the fix but, instead, starting from scratch. This approach is not at all unique to Apple. As an experienced systems person, were I to tell some customer to just "reinstall" or "restart" or similar, my customer would be unhappy and really angry when the problem returned.

If people/companies are to depend upon products such as Apple hardware and software, there needs to be a better, more professional approach to support.

I will keep updating this.

Thanks.