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Microsoft exchange email sync issues

I am having a problem with Yosemite mail, some of MS exchange emails are not sync with mail, they either don't appear in mail or the contents of the email don't appear, any help

MacBook Pro with Retina display, OS X Yosemite (10.10)

Posted on Oct 21, 2014 2:58 AM

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Posted on Oct 21, 2014 9:23 AM

Apple Mail under Yosemite is unusable for me.

We use Exchange 365. Since installing Yosemite, the Apple Mail app has decided it must fetch every single mail message and attachment that I have received over the last 4 years (even though these were already present on my Mac and available in the Apple Mail app under Mavericks). This process has been taking days. It may be that it is fetching the same mail over and over in an infinite loop. The activity window seems to show the same folders being fetched again and again.


In addition, the amount of time it takes to retrieve new mail is 3-5 minutes. Often the Mail app is out of sync with the Exchange server for hours on end. I have people complaining to me that I am not responding to their e-mails because Apple Mail is not syncing properly. My iPhone running IOS 8 does not have trouble getting new mail and staying in sync.


I have given up on Apple Mail and gone back to using Outlook Mac 2011, which works perfectly under Yosemite.

73 replies

Jan 11, 2015 8:15 PM in response to southp4w

southp4w wrote:


I resolved this same issue by opening mail > click inbox folder > click Mailbox at top of screen > click "rebuild" at bottom of the dropdown list. This should rebuild the entire Inbox and sub-folders tree. It takes a while depending on the size of your exchange mailbox, but worked fine for me. You can view progress by going to > window menu at top of screen > click "activity" and watch the folders rebuild their data...

🙂


Thanks! That did it for me. Mine was only syncing the past couple of weeks.

Jan 26, 2015 9:35 AM in response to gfelipe

The problem is that this issue will happen again, so you never know if your email is in sync or not. You have to keep rebuilding your mailbox :-(


I think the problem "may" have to do with other devices used to access exchange email...

I use O365, and since upgrading to Yosemite, my laptop mail.app client loses some emails. This seems to happen when my laptop is suspended but I still get emails on my iPhone or iPad.

Jan 28, 2015 9:27 AM in response to wer23 r2tgads

I have had a similar vexing problem with Apple mail/Yosemite for 3 months. Several times a day my Inbox, Sent and Trash were blank when I knew there was mail in all three. The temporary remedy I used to "see" those emails was to quit Mail or reboot my computer - both worked for a brief time but kept recurring.

I tried many things including appeals on this blog, contacting my ISP, cursing, praying, & begging all to no avail. I even tried re-installing Yosemite again to no avail. I have very successfully been unsuccessful!

Finally I changed a habit I had of "exiting mail" via the left top red dot and started to use Quit Mail every time I was through using it for even a short while. I also did not turn off my computer at the end of the day & just put it in sleep mode. For a few days now that seems to have resolved that issue even the continuance of putting my computer to sleep when I go to sleep. I am the sole user.

I am keeping my fingers crossed that this Quit Mail strategy will give me some peace.

You can try it if applicable & see if it resolves your problem with Apple mail.

Just like the guy who jumped off a 20 story building when asked passing the 10th floor how things are going: "So far, so good!"

Jan 28, 2015 9:47 AM in response to zaawad

So.... a couple of points of note.


I've had (and continue to have) many problems with Yosemite and Apple apps (iCal, Contacts, Calendar, etc) integration. It seems to be getting a bit better with every step.

  • Mail seemed to be helped by 10.10.2 update & Disabling (Preferences - Accounts - Exchange - Advanced - Automatically detect and maintain account settings.)
  • Calendar & contacts synch seemed to be helped by enabling (Preferences - Accounts - Exchange - Advanced - Allow insecure authentication)


I still have problems with photo support in contacts (can add from the iPhone, but doesn't update in Contacts; can't update at all in Contacts), but everything else seems to be stable across multiple machines and devices.


Note: iPhone functionality has been flawless, as has Office 365. Apple really holds the smoking gun in my opinion.

Jan 28, 2015 12:53 PM in response to BudtheSpud1

I had re-installed Yosemite about a week ago or so. Asked Ap Store for updates to OS X 10.10.1 - there were none.

I just re-checked today & found & downloaded 10.10.2. Perhaps this will help my Apple mail problems. I revert to not quitting mail,

see what happens - if all goes well, will maintain status quo. If problem seeing mail in Inbox, Sent & Trash, I'll revert to the "Quit Mail"

strategy which seemed to help.

Jan 28, 2015 3:03 PM in response to zaawad

Installed OS X 10.10.2 and Apple have still not fixed the sync problem with Office 365 Exchange account. Some emails still staying as 'unread' after being read. Have to view another folder and then come back to inbox for it to refresh and show as read. Very annoying that after 2 updates they still haven't fixed some of the basic problems.


BTW I did try deleting the Office 365 Exchange account completely and adding it again. Problem was not resolved by this.

Jan 29, 2015 12:10 AM in response to wmeyler

OK ...


I have just added a new exchange account to our system and it has zero mail or folders. I have tested this relentlessly and it works perfect with 10.10.2. Very fast does not hang no problems....


In the other account that has over 10,000 emails I have no joy. The mail app must have issues with large number of emails in exchange. Yet in Maverick mail app this is not a problem.


At this stage I am going to archive and clean my mail account. It really needs it anyhow. I'll keep all up to date on the results..


Cheers for now.

Jan 29, 2015 1:03 AM in response to wmeyler

Further from my last message. I have just found this on apples support documents after doing some digging. I will test tonight and give feedback...



Get help

If large Exchange mailboxes don't download new content

This may happen if certificate authentication is enabled on the server and your mailboxes have a large number of email messages. Microsoft recommends that you keep fewer than 5000 mail messages in Exchange mailboxes. You may see this issue with mailboxes that have more than 11000 mail messages.;

Jan 29, 2015 10:31 PM in response to zaawad

OK.... I have been on a mission for the last couple of days.


The problem seems to be with the size of the Exchange mail box and apples software inability to cope with this. In maverick it was no problem but OS X 10.10.2 does not cope with large mailboxes very well. I had 12000 or so emails and I have archived at least half to my Mac book. I then did a fresh exchange setup and bingo...It's like a new machine.


I have spent the better part of two months trying to fix this issue. I think I am finally going to resolve this. Ultimately apple should be embarrassed that not one of the software team has fixed this issue.


Its not 100% still some small bugs in mail but 99% better now..


Hope this helps

Feb 12, 2015 11:35 PM in response to zaawad

Yes, I have the same problem, I access the same exchange server from Mail and Outlook and the number of messages in my inbox is different. Mail has 838 and Outlook has over 840. Searching inbox in Mail and searching the inbox in Outlook using the same keywords show a different set of answers, the result of the former is a subset of those in the latter. Something is definitely wrong with the way Mail does synchronisation with the servers - what is it? I don't know yet.

Mar 8, 2015 6:48 AM in response to zaawad

Hi there,


I was getting a similar behaviour with yosemite native email that the exchange account for showing intermittent issue of not synchronizing the emails unless i force synchronize it or quit and re-open the application.


For now i have found a workaround for it by creating an Automator workflow application to get new mail messages (like synchronizing the mailbox) and have created a plist file as a launch agent which is doing a forced sync in the background every 30 secs and getting the emails instantly so atleast all the email messages are being synchronized without any issues now.


The workflow application is working like i am clicking on Get new mail tab in the native mail every 30 second but i dont have to do it manually but rather the launch agent does this in the background.


Hope this helps.

Microsoft exchange email sync issues

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