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User profile for user: HUWU
HUWU Author
User level: Level 1
5 points

Mail (Yosemite) not syncing all Exchange mails

I tried hard it convert from Outlook 2011 to shiny Mail. For me a disaster. Here are my problems with it:


  • Mail does not receive all mails. Some are just left out. There seems not to be any rule. Even syncing doesn't change a thing. Some mails stay at the server.
  • I send a mail and need the sent mail. I only find this in my Sent folder after a minimum of 15 minutes. Sometimes it takes more than an hour. Syncing or re-starting Mail didn't poke Mail to get these quicker from the server.
  • Although the receiving is set to be checked "automatically", it takes up to five minutes to get a new mail after it arrived on the server.


All the above don't happen with Outlook. Running both applications in parallel will always lead to MS gets the newly arriving mail first. Even a mail sent from Mail appears immediately in Outlook's Sent folder. When you are really a fan you may get around with these two. But not receiving some mails is a no go.

Posted on Nov 11, 2014 7:54 AM

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User profile for user: Linc Davis
Linc Davis
User level: Level 10
209,655 points

Posted on Nov 11, 2014 12:50 PM

Sometimes this issue is caused by a misconfiguration or incompatibility of the Exchange server, or perhaps by a bug in Mail. If so, you won't be able to resolve it yourself. The fact that your iOS devices may be working well with the same account isn't relevant, because iOS uses a completely different protocol (ActiveSync) to communicate with Exchange servers. By default, OS X Mail uses the EWS protocol.

Each of the following steps has been reported to help with Exchange issues, at least temporarily, in some cases:

1. Back up all data. Open the Internet Accounts pane in System Preferences and check to make sure you don't have duplicate Exchange accounts. If you do, delete all but one of the duplicates. If there are no duplicates, delete the account and recreate it with the same settings.

2. Rebuild the affected mailbox.

3. Reindex messages.

4. Follow the instructions in this support article to disable autodiscovery. You may need to get configuration details from the server administrator.

5. In the Keychain Access application, delete the password item for the account. The next time Mail tries to access the account, you'll be prompted for the password. Check the box to save it in the Keychain.

6. If you've created subfolders of the Exchange inbox, log in to the server through its web interface, move the messages out, and remove the subfolders. The inbox should have no subfolders.

7. Synchronize with the server using IMAP rather than EWS. This is only possible if IMAP is enabled on the server.

8. Consider using Outlook instead of Mail to access your Exchange mail.

See also this discussion.

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3 replies
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User profile for user: Linc Davis
Linc Davis
User level: Level 10
209,655 points

Nov 11, 2014 12:50 PM in response to HUWU

Sometimes this issue is caused by a misconfiguration or incompatibility of the Exchange server, or perhaps by a bug in Mail. If so, you won't be able to resolve it yourself. The fact that your iOS devices may be working well with the same account isn't relevant, because iOS uses a completely different protocol (ActiveSync) to communicate with Exchange servers. By default, OS X Mail uses the EWS protocol.

Each of the following steps has been reported to help with Exchange issues, at least temporarily, in some cases:

1. Back up all data. Open the Internet Accounts pane in System Preferences and check to make sure you don't have duplicate Exchange accounts. If you do, delete all but one of the duplicates. If there are no duplicates, delete the account and recreate it with the same settings.

2. Rebuild the affected mailbox.

3. Reindex messages.

4. Follow the instructions in this support article to disable autodiscovery. You may need to get configuration details from the server administrator.

5. In the Keychain Access application, delete the password item for the account. The next time Mail tries to access the account, you'll be prompted for the password. Check the box to save it in the Keychain.

6. If you've created subfolders of the Exchange inbox, log in to the server through its web interface, move the messages out, and remove the subfolders. The inbox should have no subfolders.

7. Synchronize with the server using IMAP rather than EWS. This is only possible if IMAP is enabled on the server.

8. Consider using Outlook instead of Mail to access your Exchange mail.

See also this discussion.

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User profile for user: Ellied02
Ellied02
User level: Level 1
0 points

Mar 27, 2015 4:12 AM in response to Linc Davis

Does anyone know whether Apple is going/able to fix this? Apple mail is now practically unusable for me at work - and I know there are many others at my work (a large UK University) that have the same issues - Mail does not pick up all the messages, takes ages to sync and is just unreliable. For me things seemed fine even after I installed Yosemite - but recently (last few weeks) it has got worse. I can use IMAP - and I think I will switch to this completely now.


It would be nice if Apple admitted there was a problem!

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Mail (Yosemite) not syncing all Exchange mails

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