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Yosemite (10.10) mail will not connect to Exchange mail server

I had participated in the Yosemite public beta, and then last night I upgraded to the Yosemite (10.10) release version.


I tested this on my MacBook Pro by updating the system in place, partially to ensure that my apps would work fine with the new OS version. All was fine except for one issue, which acts as a showstopper for me — Mail would not work with the corporate mail server (Exchange) used by my employer!


The mail account is working just fine under Mavericks, and I am sending and receiving email and calendar events just fine. But when I attempt to launch Mail under Yosemite, I get a dialog that indicates "Mail can't connect to the account "Exchange". Enter the password for xxx@xxx.com" and it prompts for the password. Even if I re-enter the proper password, it simply repeats the same dialog until I hit the Cancel button.


So, I tried the Connection Doctor, and it showed green for all accounts except the Exchange account, which has a red button and the text "Trying to log in to this Exchange account failed. Verify that the username and password are correct." When I open the detail tray and watch the contents, the exchange account is not even mentioned! So I removed all of the Mail log files and tried again and then examined the newly created log file, and the file contains the following being repeated each time I perform a test:


Oct 17 08:50:26 Doc.local Mail[1212] <Debug>: ERROR: Reading failed from socket: 0x6080004a7740, error: Error Domain=NSPOSIXErrorDomain Code=60 "The operation couldn’t be completed. Operation timed out"

Oct 17 08:50:26 Doc.local Mail[1212] <Debug>: ERROR: Reading failed from socket: 0x6000002b24e0, error: Error Domain=NSPOSIXErrorDomain Code=60 "The operation couldn’t be completed. Operation timed out"

Oct 17 08:54:50 Doc.local Mail[1212] <Debug>: ERROR: Reading failed from socket: 0x6080004bd280, error: Error Domain=NSPOSIXErrorDomain Code=60 "The operation couldn’t be completed. Operation timed out"


I een tried creating a new account using the same credentials, and I get the error "The Exchange server xxxx is not responding. Try checking the network connection, and that the server name is correct. Otherwise the server may be temporarily unavailable." This attempt results in more of the same errors as above being added to the Mail log file.


I cannot use Yosemite without this email account working, and I would appreciate it if anyone has any idea why the same settings (shared via iCloud) continue to work without issue under Mac OS 10.9.5 and iOS 8.0.2 (iPhone and iPad) but fails under Yosemite. Is there a setting I can change somewhere? Vey odd.

MacBook Pro (15-inch Early 2008), OS X Yosemite (10.10)

Posted on Oct 17, 2014 6:05 AM

Reply
29 replies

Oct 19, 2014 2:56 PM in response to Ken.Allen

I looked at your problem because i thought it might help mine. I have a local mail server using postfix and popper that worked fine under Mavericks but Apple Mail under Yosemite says the connection is being refused on the default port, 110. What's interesting is I can telnet to "localhost 110" with no problem. The problem seems to be with Apple Mail. I had hoped you had a solution.

Nov 17, 2014 1:37 PM in response to Ken.Allen

Has the Yosemite update (10.10.1) fixed it?

"The OS X 10.10.1 update is recommended for all Yosemite users. It improves the stability and compatibility of your Mac. This update:

...

- Improves reliability when connecting to a Microsoft Exchange Server

...


Exchange is still working fine for me. I had problems with Mountain Lion but this was fixed when my Exchange service provider did an update.

Nov 17, 2014 2:01 PM in response to Michael Paine

I have not yet updated to 10.10.1, but the issue was actually resolved by the IT group 'tweaking some settings', but they did not indicate which settings.


I am hoping that 10.10.1 may resolve the issue where most of the time deleting a message does not remove it from the smart mailbox list right away, but it is gone if one select another mailbox and then back again.

Dec 1, 2014 10:46 PM in response to Gman2112

See these tips from when some of us had problems with Exchange and Mountain Lion:

http://premnair.wordpress.com/2010/07/03/configure-ews-autodiscover-owa-oab-ecp- on-exchange-server-2010/

(an old Apple discussion at Exchange under Mountain Lion )


I no longer have problems with Exchange. I did refer that link to my Exchange IT person but I have no idea if this helped them fix it (in September last year).

Dec 3, 2014 5:18 AM in response to Michael Paine

Thanks for this Michael - Checked this all out and our auto discover is configured correctly. Strange thing after reading through the other discussion you linked to is that I never had an issue with Mountain Lion, had an issue on calendar and contacts (but not mail on 10.9.x) and issues with all 3 on 10.10.x without changing any settings.


Will keep playing around and let everyone know if I stumble upon the solution. Again, bizarre (as everyone else has noted) that it I have no problems on iPhone or iPads.

Dec 3, 2014 8:20 AM in response to Gman2112

I spoke with our IT group and the following is the response I received:

In a nutshell, very little was done on our side. We confirmed that we were on the latest patches for our Exchange servers. We also verified that the OWA/Client servers were configured per best practice. What was discovered actually landed on the Apple side.

First - The release build of Yosemite appeared to be reading the auto configuration details for Outlook Anywhere incorrectly. This information contains the name of our servers both internally and externally. Yosemite was attempting to connect to the internal server name, which of course would fail unless the device was connected to our corporate VPN. I believe this was corrected in an update for Y0semite that was pushed out a couple of weeks ago so make sure that they are on the latest Yosemite patch.

Second - The credentials used for accessing our email servers must contain the domain name as well as the user name (ecisolutions.com\username). If a current internet connection for Exchange shows only the username then that connection will fail. The easiest way to correct this is to delete the internet account and create a new one using the correct format. The current connection can be modified but it is a bear to get to.

I'm not exactly sure what changed that caused the second issue to appear. As I mentioned, there wasn't a lot on our side that we had to deal with.

Dec 3, 2014 9:56 AM in response to Ken.Allen

Thanks for digging, Ken -


Took a shot at what you described, but still to no avail. I'm starting to wonder if it is something on the Exchange side of things. With the latest settings (making sure external and internal servers are the same and correct (in fact, settings across the board are pretty much identical to what is working for me in outlook)) I get the following errors when clicking on the caution symbol showing that the server is not connecting:


In Mail:

The server returned the error: Connections to host www.xxxx.com on the default ports failed.


In Mail Connection Doctor:

Could not connect to this Exchange server. Check your network connection and that you entered the correct information in the Account preferences. Also verify that the sever supports SSL. If it does not, deselect the "Use SSL" checkbox in the Advanced tab of Account preferences.


In Calendar:

The email address "xxxx@xxx.com" isn't a valid address for your Exchange account. Enter the email address for your Exchange account, and then click OK.


In Contacts:

The operation couldn't be completed. (SOAPWebServicesErrorDomain error -1.)


So at least it's exciting that I get different error messages across the board!

Dec 10, 2014 7:49 AM in response to Ken.Allen

I have the same problem. My apple mail connected to the exchange server was working fine in mavericks, still works fine on my my home computer (did not upgrade yet. As soon as I upgraded to Yosemite, I get invalid username and/or password. I have tried everything.


The account settings are identical between my mavericks mac mini and my Yosemite macbook air but the Yosemite does not work and the mavericks does not.

Dec 15, 2014 2:50 PM in response to mhoadley

Don't think this is related since it looks like you can connect in the first place.


In the past I've noticed that any text that is written in the message below an attachment (especially images) gets lost when sending to PCs. Make sure you have the following options selected, both in the Edit menu on Mail.


  • EDIT -> ATTACHMENTS -> Send Windows-Friendly Attachments
  • EDIT -> ATTACHMENTS -> Insert Attachments at End of Message


That solved it for me. Good luck -- and congrats on being able to send partial messages, at least!

Jan 21, 2015 2:52 PM in response to Gman2112

I am having the same problem


In Calendar:

The email address "xxxx@xxx.com" isn't a valid address for your Exchange account. Enter the email address for your Exchange account, and then click OK.


In Contacts:

The operation couldn't be completed. (SOAPWebServicesErrorDomain error -1.)


Has anyone found a solution for this? I have removed and added my exchange account so many times I cannot remember and there is very little information about this particular problem.

Mar 16, 2015 6:47 AM in response to turkito

Hmmm I can connect to Exchange, Contacts/Calendar/Mail working at first.


Then, intermittently, Calendar and Mail throw up the "Enter Password" modal box, and the connection to Exchange is lost. Closing Mail/Calendar/Contacts and waiting 15 Minutes clears the problem.


In the console, I see


16/03/15 14:42:36.810 Mail[1565]: Stream 0x60800050e8e0 is sending an event before being opened


and


16/03/15 14:37:39.593 Mail[1565]: Received undocumented error: The meeting message couldn't be correlated because the target is a repeating master and the meeting message is an occurrence. on EWS response <MFEWSGetItemsResponseOperation: 0x6000002be7e0>{name = '(null)'} (EXECUTING)

16/03/15 14:37:39.594 Mail[1565]: Recieved EWS error: Error Domain=MFEWSErrorDomain Code=141 "The meeting message couldn't be correlated because the target is a repeating master and the meeting message is an occurrence." UserInfo=0x608001876a80 {NSLocalizedDescription=The meeting message couldn't be correlated because the target is a repeating master and the meeting message is an occurrence.}


I have absolutely no clue, how I should find these conflicting meeting messages, why Mail and not calendar is complaining about it, and if this is even remotely related to the password problem.


Does anyone know more?

thanks

simon

Yosemite (10.10) mail will not connect to Exchange mail server

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