Mail issue with MS exchange server on macOS Catalina

The only work-around that's worked for me is to use Mac Mail in one device and Outlook on the other.

Hello kindenk,

Thanks for the update. Did the issue remain when you tried safe mode and another user account? If the issue remains and the issue still persists intermittently, you'd want to reach out to Apple Support for further assistance.

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I use my Macintosh for both personal and work. It is my system.

I have had been using Apple Mail as my unified email client for many years, with aboutSince upgrading to Catalina, with 7 POP and 2 IMAP and 1 Exchange accounts. I have about 70k messages organized into I don't know how many local mailboxes (including emails migrated from my UNIX days). The client is set to check email once per minute. I have been running relatively problem free for most of that time. Occasionally, the client would, for some unknown reason, lose a password despite it being in the keychain. Who knows.

But, with Catalina, with the 10.15.0 release, all **** broke loose. Exchange stopped work at all; I had to use Microsoft's Outlook client. My POP services started sending me emails saying my client was logging in multiple times per second and that they would temporarily shut me down if it kept up (it did and they did). Or, the services would send me emails that saying that there were too many failed logins so, for security, they have disabled my account.

10.15.1 got slightly better. 10.15.2 is relatively stable but I am still occasionally getting those errors from my POP service providers and Exchange does not work well..

The Exchange capability on the Apple Mail client is still problematic. The Apple client seems to fail to update the Exchange service when messages are read or deleted; however, it does get updates when messages are read or deleted by the Microsoft Outlook client.

Completely deleting the Exchange account and adding it again does seem to, as others here have said, restore operation - for a while.

Bottom line: Apple has damaged one of the most critical utilities on MacOS. There needs to be much much better QA on such an important tool.

I hope 10.15.3 is better.

I also have had this issue. It persists after safe mode and change login user to test. It definitely only occurs with my exchange server. All the other non-exchange accounts work perfectly. If I set up MS outlook, canary mail or postbox they all work fine and do not have this issue.

Really disappointed that Apple continues to ignore this issue. Very unsatisfied.

Hello everyone.

I lost an email in macOS mail app last week. So that was the last straw for me. All I was doing was moving it back to the inbox it came from after archiving it within a folder on my Mac. The message vanished, but luckily there is some built in 30-day protection for Office 365 hosted Exchange accounts. I was able with MS supports help to recover the email.

Anyhow I wrote and email to Tim Cook and Apple responded. Thank goodness. I rely on Mail and all these problems we are having are disheartening.

So I strongly suggest that all of you open a case with AppleCare, submit Feedback on Apple's website or even better submit a bug report. I've gotten their attention. Help me to keep it!! Speak up!!!

Thanks!!

Am having the same issue on two computers running Catalina - MacBook Pro and iMac. Apple Mail shows new email messages on my exchange account and syncs read status and folder changes made in Outlook or on iOS devices, but changes made in Mail don't sync back to the server and aren't reflected in Outlook or on other devices. This is only happening with Exchange.

Messages sent on the Exchange account in Apple Mail also don't appear to actually be sent, and aren't showing up in the sent folder on Outlook.

Running macOS 10.15.1 on both computers.

Have tried deleting the Exchange account and reading it, but it has not made any difference.

I'm having this issue as well, or something related to it . As of last Wednesday (maybe Tuesday, Dec. 17?) Inbox messages that I delete using Mac Mail suddenly stopped getting deleted from the Exchange server.

Messages deleted on my Gmail account using Mac mail are deleted from that server without issues. I also can delete messages from the Exchange server using iOS devices and this deletion is updated in Mac Mail. 

Filing messages from the Exchange server into a Mac Mail folder does put the message in the local folder, but the action doesn’t remove it from Exchange Inbox. So it seems to be a Mac Mail/Exchange specific problem. 

The problem started under Catalina 10.15.1, and persists after upgrading to 10.15.2. Running a 2018 MacBook Air retina.

Right now, I have to read/compose messages on my iPad, go to my Mac to file them, and then return to my iPad to delete them. *Very* cumbersome, particularly with a 100+ email/day volume. Any suggestions are most needed/welcome...

Thanks.

I have this same problem now for months. All I can say is if you haven't open a ticket with AppleCare like I have to get some light on this problem. It's bad enough that I'm thinking about finding a replacement for Mail app in macOS.

Thanks for the feedback. I did enter a feedback request- with no response from apple. I finally called apple and asked for a case and just begun going through the process of troubleshooting. One of the things they asked me to do, is disable MCafee. I will the solution above, and would appreciate if you posted back and let me know how the exchange account behaves during the course of the week.

I have been completely frustrated, and apple looks at accounts added in apple mail as a pass through and a quick to point to the mail provider.

I would like to know the root cause of the behavior.

After doing all of that, are you still having problems lauener ?

When i take a mac on a previous OS, and add my exchange /office 365 account, I don't have any issues. I was getting ready to create a new account and see what happens, I am at that same place, create a new account and remove McAfee after a capture of logs on apple mail is the advise they gave me.

I told them a few others have the same problem, are you asking us to do this to all affected machines? he went to check and never got back with me.

I agree that this is not a fix. To ensure we are meaning the same thing with the given terms, I have reconfigured Mail with the email (Exchange) account several times. This is the first time I have created a new login on MacOS and then grew my environment from scratch, moving/copying as few things as possible.

At least, this is a first time for me. We will see. Again, I share your frustration that this is not a fix. Bit-rot problems are hard to find. But, without significantly more diagnostic tools and knowledge, this is the approach with which I am left to try. I have said as much in my post of last night.

Yes, I install brand new systems for a profession and it does not matter after a few months this always happens again and their are no diagnostic tools. I buy a new machine, new employee and it always happens again. This has been an issue for many years. I have started steering everyone to Outlook because this does no happen with that client. However, people love the Apple mail client, I acknowledge that, and just want Apple to admit there is an issue and that they are looking into it; that has never happened. I simply want to be able to support people who use the Apple client in a professional environment. Please keep us all posted maybe Apple has fixed "it" and the issue will not occur again.

Unfortunately I experience the same problems. Creating a new user-account only helps temporarily. I sincerely hope Apple will fix this problem and/or the problem will be fixed with the new Mac OS coming this fall.

It is variable - I last created a new account 2-1/2 weeks ago and it just started acting up yesterday - mail moved from an Exchange account to an iCloud folder does not show as moved on other machines (message(s) are still in the Exchange account on iPhone, iPad and MacBook) - also I've noticed that when this problem starts getting new mail from the Exchange server seems intermittent across my multiple devices. Creating a new user account, setting up and downloading everything (photos, iCloud, mail, etc.) is a time consuming and painful process.

I have a similar problem.

3 days ago we updated one of the Macs in our office to Catalina. We all use Exchange email and we have two accounts that we all access on 2 Macs and 1 PC. The Mac we updated is still sending and receiving emails via Mac Mail just fine, and on that device any sent items are going to the sent items folder, and read mail shows as having been read. Also any items moved to a folder appear correctly on that device.

However, on the PC (running Outlook) and the other Mac using Mail, the inbox is not appearing as having been updated. So anything read on the suspect Mac does not appear as read elsewhere (nor, presumably, on the server), and sent items from that device are not visible as sent items on the other devices. Also, anything moved to a folder/mailbox on the suspect Mac do not show up in the folder elsewhere (although, strangely, new folders created on the suspect Mac do appear on the other devices.

Any ideas?

Thanks