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Level 1

5 points

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

29 replies

h27th

Level 1

0 points

Apr 2, 2015 5:31 AM in response to Ken.Allen

Same problem here. Using Yosemite 10.10.2. I'm 100% sure that I use the correct credentials.

Point is that the Exchange configuration on my iPad 2 (iOS 8) and iPhone 5S works just fine. No problem there.

So: what's different in OS X? Except that the dialog box for an Exchange account doesn't mention the Domain? iOS does.

Apr 12, 2015 12:06 PM in response to h27th

Same problem here - updating to 10.10.3 didnt change anything.

I am using 3 Exchange accounts on iMac and iPhone. Two of them do ask for credentials, one is still fine. Same server, same domain, different email adresses.

Accounts still work on iPhone 4s and MS Outlook 2011.

Any idea?

j.ffm

Level 1

4 points

Apr 22, 2015 1:37 AM in response to zaxxon72

Same here ... seems like a problem related to reoccurring events in the calendar.

Is there any way to get rid of the action item that causes the error log messages?

Oscar_7

Level 1

8 points

Apr 26, 2015 2:30 PM in response to Ken.Allen

Exact same problem here. I can connect just fine using iOS, but OS X 10.10.3 fails to login to my work's exchange server

kkp12

Level 1

4 points

Apr 28, 2015 5:33 AM in response to Ken.Allen

Same thing started happening to me last night. I am so sick of Yosemite. Nothing but problems and no sign that Apple is interested in resolving these issues. I feel like a windows user again.

May 26, 2015 11:07 PM in response to Ken.Allen

Same here, Mail and Reminder work, calendar don't sync. Hopefully waiting for an update, maybe bevore 10.11 :-(

Jun 19, 2015 4:54 AM in response to Michael Re.

I have the same problem and it is really screwing up my operation. Come on Apple, get this fixed as it has gone on long enough. I have always expected problems with Microsoft but lately Apple seem to be trying to catch them up in this area! Does anyone know about going back to Mavericks? I wish I had never upgraded!

KiltedTim

Level 10

195,573 points

Jun 19, 2015 5:13 AM in response to kkp12

What version of Exchange Server is your organization running?

Jun 22, 2015 3:33 AM in response to KiltedTim

The server is provided by a 3rd party and is running on Exchange 2010.

Jun 29, 2015 4:02 AM in response to KiltedTim

I can see you are busy but did you get my response KiltedTim.

Klohmann

Level 1

0 points

Jul 29, 2015 5:38 AM in response to regor gnillib

Same here. Profoundly disappointing on the part of Apple.

Aug 4, 2015 1:22 AM in response to Ken.Allen

I don't know if this answers your specific problem, but I found my Exchange account would not work on Yosemite and was stumped.

Then, Office365 sent an automated mail telling me that 'one or more of my mailbox folders is named incorrectly'. In my case, they had the '/' character. Once I renamed the folders, the Exchange account set up fine.

diegoCAS

Level 1

9 points

Oct 10, 2015 7:11 AM in response to Tetrachrome

Same problem here, had to return to Outlook, which is quite awfull.

What I was able to discover here, is that this is probably related to the "\" backslash use for the domain\user credentials, and how apple mail shows it to the Exchange server.

After SOAPRequest Exchange server returns

Error Code: 500 Internal Server Error. The request was rejected by the HTTP filter. Contact the server administrator. (12217)

This could be related to an incompatibility between exchange, microsoft firewal (IIS) and apple mail.

With same credentials outlook 2011 for mac works perfectly.

So Apple, please solve this. On Yosemite, and if the fix is available moving to El capitan please, let us know. But be sure.

Oct 17, 2015 10:36 AM in response to Ken.Allen

Same problem here! I wish I never updated To Yosemite 😟

@Apple: PLEASE fix this problem!

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