Strange New Mail Bug?

[Adult80HD]

I'm curious if anyone else has seen this. This is a new development for me but poking around over on the Apple support forums I've seen one or two other reports of this.

About two days ago Mail suddenly stopped syncing regularly with my hosted MS Exchange through Office 365. What's weird is that the account setup shows it's fine and connected, and I can send mail with no problem. The inbox just doesn't update to show new messages except at random intervals. Interestingly enough, other folders will do the same thing--sometimes the Trash folder will update or the Junk folder, while the Inbox remains out of sync.

I thought it was a 10.15.6 Beta problem, or something with my account. I have tried deleting the account and totally recreating it. It syncs once, then it stops. Today one of my employees reported the same problem, and they are of course using their own email account on the same server, but the iMac they are using is on 10.15.5.

If I use Outlook, everything works fine, but I dislike Outlook--a lot. It's all fine on everyone's iPhones, too, so it seems like it's not a server issue on the Microsoft side, but something odd with Mail itself.

Is anyone else using Exchange and experiencing anything like this?

 

[Zach_]

My Macs stopped syncing with Office 365 today at about 1:45pm. I've since deleted the internet account from two systems and re-added them, but that hasn't helped. FYIW, I'm running 10.14.5.

In Mail's Connection Doctor, enabling the logs creates a log file for account "(null)" and the file size is zero bytes.

Something is severely broken with either iCloud or Office 365.

 

[Adult80HD]

My Macs stopped syncing with Office 365 today at about 1:45pm. I've since deleted the internet account from two systems and re-added them, but that hasn't helped. FYIW, I'm running 10.14.5.

In Mail's Connection Doctor, enabling the logs creates a log file for account "(null)" and the file size is zero bytes.

Something is severely broken with either iCloud or Office 365.

OK so I started seeing it yesterday afternoon some time. If I rebuild the inbox, it updates, but then it immediately goes back to not updating at all.

 

[Taz Mangus]

OK so I started seeing it yesterday afternoon some time. If I rebuild the inbox, it updates, but then it immediately goes back to not updating at all.

I would suggest try creating a new clean user account and setup the e-mail in the new used account. See if the issue still happens in the new user account.

 

[Adult80HD]

Interesting update: Last night I did a rebuild of the mailbox. The mail all came in and I thought I had it solved...but then it stopped syncing. I could make it sync by repeatedly doing mailbox rebuilds, but it wouldn't sync on its own.

This morning, everything is working perfectly. I've had both Outlook and Mail open and they are both remaining in sync. Either MS had a problem that only effected Mac Mail users or Apple had some issue (although I can't see how?), but it *appears* to be resolved.

 

[Wayne Vineyard]

Well, this problem seems to have cropped up again with Outlook 16.42. I am running Mac Mail on Catalina with no problems for months then the Outlook updated and my Mac Mail Inbox won't synchronize. All the other folders; like Sent or Trash, update just fine. If I delete my Exchange account and then add it again, I get any new emails. But nothing will synchronize after that.

Anyone else seeing this crop up again?

 

[leonchu1225]

Same thing happened to me this week. I was guessing it could be the update of macOS 10.15.7 did this. As I knew I updated this version about a week ago, but can't be sure.
Didn't notice the update of Outlook. I wasn't using it, but did install it when I installed Office365 years ago.

Nothing worked for me. Apple Support was helpless. Asked me to grab bunch of data and just asked another rep to call me back. Check the Connection Doctor I checked 100 times and told me it's 365 server issue.

Tried rebuild the mailbox. Download kept stopped itself and I had to restart Mail multiple times. I have about 30,000 emails over the years and it took me 3+ days to get everything done...yet the issue is still there.

I also read an old Apple support link claim the Exchange mailbox can't go over 10,000 messages, but I don't think that's the issue, as my Mail was all ok before this week. Still, I moved a lot of those 30,000 emails to Archive (with Outlook as it's more stable and reliable atm) and now re-downloading those emails again.

iOS mail. Outlook on Mac (now I have to check the email with this. Still don't like it, but at least it's reliable so far). Spark on Mac all ok. Gmail and other accounts all good.
Tried everything I could find online (thus see this post) and nothing worked so far.
My guess was the Mail issue (due to the upgrade), O365 server issue (they changed something on their end and Mail stopped working).

The only thing that is remotely helpful is the click Shift when opening Mail. It goes into Safe mode according to Apple Support (not much diff I can notice compare to normal mode) and the download/sync is slightly more reliable. Still not normal though.

I guess I would have to hoping Big Sur would fix it or it's O365 server issue and they fix there.
Any suggestions would be appreciated!

 

[gogogut]

I am having this problem with Mac Mail connected to a work gmail account. Everything works fine if I login to the gmail account in a web browser. I see and can interact with all my messages. But the Mail app has serious sync issues for a couple days now. For hours it tells me I have no email, so I quit and start back up to see lots of missed emails. Then when I try to view them, I get Loading with the spinning gray circle. Sometimes the emails appear after some time, but it is nearly impossible to read and interact with email. If I compose a message and send it, there is no problem. I need a fix ASAP!

 

[leonchu1225]

I am having this problem with Mac Mail connected to a work gmail account. Everything works fine if I login to the gmail account in a web browser. I see and can interact with all my messages. But the Mail app has serious sync issues for a couple days now. For hours it tells me I have no email, so I quit and start back up to see lots of missed emails. Then when I try to view them, I get Loading with the spinning gray circle. Sometimes the emails appear after some time, but it is nearly impossible to read and interact with email. If I compose a message and send it, there is no problem. I need a fix ASAP!

I have 2 gmail accounts and both of them are all normal. Not sure if your work gmail account has any special setting on the server side. My work O365 account also is fine with sending email. Just don't pull in the email so I miss many work emails (that's terrible). Hopefully we get a fix soon.

 

[vett93]

I have similar problems with Yahoo mail messages. I have 5 email accounts on my Mac Mail. The problem only exists with Yahoo mail. Mac Mail would work for a day and then stop retrieving messages from my Yahoo account. If I quit Mac Mail and start it up again, it would work another day and stop again. I can retrieve Yahoo mail using web reliably. I have contacted Apple and Yahoo support and cannot resolve the problem. The problem seemed to start 6 months ago and it worked fine before that.

 

[Jimmy Padia]

It crazy, I am facing exact same issue in Mac mail - since last 2 days, that too only for 1 O365 exchange email. I have 3 other 365 emails configured in same Mac mail and they are working fine.
This is weird issue, in Mac mail
Everything works fine in outlook and web browser, but I hate using them,

Apple, what are you messing up?

 

[aroubini]

This summer, I experienced this with a customer and for myself within literally a week of each other both, both starting and ending in sync. Both of us had Microsoft 365 business email accounts, but were on completely different domains. I couldn't find any info on what might have been happening back then, and even opened up support cases with Microsoft. No resolution was found.

The matter cleared itself up after a week and a half of hell trying to get my client back up and running on his Mail program to little avail. Throughout all of this Outlook was a solid backup—but I couldn't wait to get back to Mail.

Now this week it's happened again. NO connection errors nothing, just all of sudden my Mail on my MacBook and on my iMac went down—completely stopped downloading any new email. As before Outlook and iOS work fine.

If it plays out the same way, my client might well be heading for another storm.

I could only conclude it was some certificate issue, but could never get to the root of it.

 

[kohster1]

Glad I found this thread. I had the exact same problem with my work Microsoft 365 Exchange account back in December. At the time I was running Catalina, and Apple Mail.app wouldn't automatically get any of my Exchange mail. Outlook running on the same computer was fine, as were the iOS and iPadOS 14 Mail clients. If I opened a specific folder on the Catalina Mail.app, then that folder would get synced just fine and download any new messages.

A couple days after that, I'm not 100% sure if this is related, but I got an autodiscover message in Outlook saying that i was moving to another mailbox server, and very quickly after that, Mail.app started automatically downloading Exchange mail again! Totally not sure if those events are related.

Over the holidays, I upgraded from Catalina to Big Sur on my Mac. Then this past Monday, the problem reoccured.

I had opened low priority tickets with our email and support folks just to see if anyone else had reported a similar problem, but apparently I'm the only one. If we were still running on-premise Exchange, the email folks would have been able to shift my account around to different mailbox server just to test the above hypothesis that the autodiscover message and the restoration of services were related, but apparently once you're in the cloud with Microsoft 365 a lot of those controls and visibility go away, so they really can't dig really deep to figure out what's going on either.

 

[kohster1]

I think things started working again this morning. No mailbox server change message in Outlook though. The only significant thing I changed is that over the weekend I deleted a couple of really old mail folders with a few thousand messages. I wonder if I’m just hitting some internal limit on how many messages can be associated with an account….

 

[DrNathaniel]

Mine started with this two days ago. Same symptoms: wont' update. Removing/adding doesn't help. "Rebuild" on the inbox reveals new email.

Local IT useless, except that they say that Mac Mail is not supported and won't correctly authenticate... which is clearly BS. Tell me to use Outlook. Bleah.

One interesting datum: I had connection logging on, and had log files like "smtp.office365.com-XX...XX.txt". Those are no longer updating, but an empty file has appeared labelled "(null)-XXXXXXX...XXX.txt". I have no idea what that portends though.

 

[corinburr]

Have the same problem - emails wont arrive in the inbox unless I do a Mailbox Rebuild which then brings it up to date. I have tried deleting the Exchange account from Internet Accounts a few times over the past few months - this has temporarily sorted the problem but the issue always returns. Tried a clean install (not from backup) - again works fine for a few weeks then the issue returns.

This issue doesn't exist on any iOS devices; and works fine on Outlook for Mac so clearly a Mac OS issue. Have this issue on Big Sur 11.2.1.

 

[BrianBaughn]

Office 365 email set up as Exchange in Mojave hasn't been an issue here.

When any internet-based service has connection issues for me on any device I always suspect DNS problems.

 

[bruce.desertrat]

I now have two people having this issue. (I do IT for a college; we have O365 for our email). Same symptoms as people mentioned above: Mail works just fine, then stops properly synching. One person has the problem only on his work desktop iMac. His laptop and iMac at home (all running the same OS version: Catalina 10.15.7 ) work just fine. I get my mail on four different macs from two different O365 accounts and never have this issue.

I've rebuilt the affected mac from scratch...he was ok for a week, then it started back up.

It's been enormously frustrating to try to reproduce the bug because it'll work one day and not the next.

 

[shario83]

I had this problem a few months ago, rebuilt Mail and started working again, but today, it has stopped synching again.
I am on macOS Big Sur version 11.2.1