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Mail issue with MS exchange server on macOS Catalina

Since upgrade macOS to Catalina, my mail is not able to move mail on exchange server to local mail folder, also all the read mails from Mail is not changing it status.

there is no problem with iOS 13, so I from my iPhone I can still see those mail I have moved to local folder or read using MacBook are still on exchange server.

MacBook Pro 15", macOS 10.15

Posted on Oct 21, 2019 6:28 PM

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Posted on Dec 19, 2019 9:47 PM

@John P.

I tried this several times and I am talking about issues with MS Exchange server not about Exchange (Office 365).


A not efficient workaround is, to delete the exchange account on the MAC completely, then create it new. This works then for several days, than this workaround has to be repeated. With a large E-Mail-Database this takes quite a long time, and some E-Mail attachements are most of the times lost afterwards.

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Dec 19, 2019 9:47 PM in response to JohnBradshaw

@John P.

I tried this several times and I am talking about issues with MS Exchange server not about Exchange (Office 365).


A not efficient workaround is, to delete the exchange account on the MAC completely, then create it new. This works then for several days, than this workaround has to be repeated. With a large E-Mail-Database this takes quite a long time, and some E-Mail attachements are most of the times lost afterwards.

Oct 28, 2019 8:47 AM in response to kindenk

Hello and welcome to Apple Support Communities kindenk,


I see that you're having an issue with mail since updating to macOS Catalina. I understand your concern, and I'd be happy to help.


Let's start by trying a couple steps to try to isolate this issue further. First, try starting your Mac in safe mode and then testing to see if the issue remains. If needed, the first link listed will guide you through starting up in safe mode. If the issue remains in safe mode, then the next step you can try is testing in another user account. The second link will guide you through those steps, if needed.


Use safe mode to isolate issues with your Mac


How to test an issue in another user account on your Mac


Let me know how this goes.

Have a great day!

Dec 19, 2019 10:03 PM in response to MacMichael64

MacMichael64 wrote:

@John P.
I tried this several times and I am talking about issues with MS Exchange server not about Exchange (Office 365).

A not efficient workaround is, to delete the exchange account on the MAC completely, then create it new. This works then for several days, than this workaround has to be repeated. With a large E-Mail-Database this takes quite a long time, and some E-Mail attachements are most of the times lost afterwards.


Acknowledged. When you say large e-mail database, exactly how much mail do you have in your Exchange account? --Have you tried IMAP as a test or workaround?


The reason I ask is this may be relevant...

"If certificate authentication is enabled on the mail server, make sure that your mailbox has no more than 11,000 messages. Microsoft recommends no more than 5000 messages per Exchange mailbox."

https://support.apple.com/en-us/HT201951




Jun 21, 2020 11:30 PM in response to kindenk

I have been suffering, with all of you, the problems of Catalina Apple Mail and Exchange.  I have included my reports to Apple via Feedback in the “additional text.”


I am writing today to report a potential solution.


On Thursday, I rejoined Apple's JointVenture support plan.  I had purchased this previously but let its subscription lapse.  For this single primary email problems reported here (my 1/28/2020 report in this thread), I rejoined at a cost of $500.  I scheduled a service call for Friday afternoon.  I was connected with a senior support person known to me only as Rebecca.  She was knowledgable and did not talk down to me.  It was actually quite pleasant.  She proposed the solution described below.


As an aside, there was one additional problem I did not report: Apple Mail did not adhere to the "check for new messages" preferences setting.  Regardless of whether I set to check the servers ever 1 minute or 5, once or twice an hour, Mail would connect to the server in much shorter intervals: as reported by one of my POP services, 1 connection every 0.1240 minutes (7.44 seconds)!!  At about the same time, my service had updated their software so I wasn't sure who the offender was/. I finally sniffed the network and found that Mail was indeed coming in at sub-minute times between checking.


So, where am I going with all this?


All of the problems I experienced and reported in this thread have been fixed, including that one I did not report.  At Rebecca's suggestion, I created a new user on my system and, once logged in, created a new Mail Exchange email account.  I did the same for MS Outlook.  As I had before, I ran them side by side.  As I read an email in Apple Mail, within a few seconds, the email entry in Outlook changed from unread to read.  When I deleted a message or moved it to another folder (on my system), the message disappeared from the list on Outlook.  Outlook even reflected the flagging (though I didn't check for proper colors).


The rest of my 570k email messages spread in various mailboxes were exported from Mail in my old login and transferred to and imported to Apple Mail in my new account.  As I keep all of my files (including photos and music) in a separate directory in /Users, the rest of the migration wasn't that painful.  I avoided the migration utility or wholesale copying of stuff to avoid unnecessary and potentially troublesome state from coming over.  I can detail more how I run my systems if anybody is interested.


My login on my Catalina has evolved through manual copying and eventually Migration Assistant from my earliest days on a Mac (I converted from UNIX to Macs in 1991).  I could see older pref files and who knows what else.  So, this maybe was a good thing to do - a little rebellion now and then is a good thing.  As a side benefit, the fan on my Mac runs MUCH less than it had - subjective but noticeable.


I have been testing this solution as I enabled more and more of my environment (licenses, passwords, etc. for other applications) and little widgets (MenuMeters, JAC, Grabbit, FSMonitor, Microsoft Office products, etc.).  So, for the most part, I'm pretty much up and running.  But, the real test will come over the next several days during high activity on the Work Exchange server and me being tied to doing real work (MS Teams, etc.).


Other potential suggested fixes here have lasted a few days, if at all.  So, if, by the end of this week, things are still working fine, I will declare victory and recommend more of you create a new account and start from fresh.


Sorry to be so verbose but this has been a significant pain for too long a time.  My one regret is that there isn't enough information available in the system (or, seemingly, experience outside of Apple Engineering) to really debug and find the problem.  But, if we are through this gauntlet, wonderful.


For what its worth, I will report back here near the end of the week (or sooner if the situation regresses).


   aps


Configuration:

MacBook Pro (16-inch, 2019)

MacBookPro16,1

Memory: 16 GB 2667 MHz DDR4

Graphics: AMD Radeon Pro 5500M 4 GB

Intel UHD Graphics 630 1536 MB

Storage: 2 TB flash

Displays: Dual (side-by-side) 27" Thunderbolt Displays

Thunderbolt to USB-C adaptor


This system was purchased in March; the same was occurring on my previous MBP, a Mid-2017 MacBookPro14,3.

Jun 15, 2020 4:19 AM in response to kindenk

At some point after installing MacOS Catalina I started having issues with my school's Exchange server: specifically my Apple Mail app wouldn't update its inbox with incoming messages. I found this thread but couldn't quite get an answer that would provide a stable solution. The following advice given to me by our tech support proved very helpful in my case:

  • Open the System Prefs and select Internet Accounts
  • Select the Exchange server, click on Details, delete the currently inserted password and then re-enter it

I know it sounds like voodoo but it solved my problem (4 days without a problem) so it might be worth to give it a try.

Jun 22, 2020 8:39 AM in response to Armando Stettner

I also have had this issue.

It definitely only occurs with my exchange server and Apple-Mail.

Deleting the account and Add it again will help - for some hours, sometimes for some days.


I did the same things you did, Armando

  • created a clean new account
  • added my exchange-account
  • added my Apple-Mail Account
  • and migrated all mailboxes


Apple Support told me to test it with a new user. I am not amused. All these settings.

Nov 6, 2019 8:04 AM in response to kindenk

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

Nov 26, 2019 9:42 AM in response to thirstycol

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!

Dec 1, 2019 12:38 AM in response to lgustavomartins_iCloud

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.

Dec 5, 2019 9:36 AM in response to lgustavomartins_iCloud

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...

Dec 19, 2019 8:48 PM in response to kindenk

I was having some minor niggles with Apple Mail + Exchange (Office 365) but v10.5.2 seems to have resolved at least the perceivable ones.


Try setting it up in a alternate user account, just to test it. Setup a bogus Administrative user, and once logged in setup the Exchange account. If the issue is resolved, it's likely a compromised preference file or Envelope index.

Mail issue with MS exchange server on macOS Catalina

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