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Mail slow authenticating to Yosemite server

I'm running mail on a Yosemite server, and Mac Mail client on Yosemite. With the "Activity" window open on the Mail client, I see two copies of "Communicating with server: Authenticating" a lot. On the server /Library/Logs/Mail/mail-err.log is filled with lines:


Nov 06 10:58:06 auth: Error: od(simon,192.168.0.29,<MuZNkS4HfQDAqAAd>): Credentials could not be verified, username or password is invalid.

Nov 06 10:58:06 auth: Error: od(simon,192.168.0.29,<MuZNkS4HfQDAqAAd>): authentication failed for user=simon, method=DIGEST-MD5

Nov 06 11:00:12 auth: Error: od(simon,192.168.0.29,<suuzmS4HggDAqAAd>): Credentials could not be verified, username or password is invalid.

Nov 06 11:00:12 auth: Error: od(simon,192.168.0.29,<suuzmS4HggDAqAAd>): authentication failed for user=simon, method=DIGEST-MD5

Nov 06 11:00:18 auth: Error: od(simon,192.168.0.29,<BLfTmS4HhADAqAAd>): Credentials could not be verified, username or password is invalid.

Nov 06 11:00:18 auth: Error: od(simon,192.168.0.29,<BLfTmS4HhADAqAAd>): authentication failed for user=simon, method=DIGEST-MD5

Nov 06 11:00:28 auth: Error: od(simon,192.168.0.29,<okUwmi4HhgDAqAAd>): Credentials could not be verified, username or password is invalid.

Nov 06 11:00:28 auth: Error: od(simon,192.168.0.29,<okUwmi4HhgDAqAAd>): authentication failed for user=simon, method=DIGEST-MD5


In the Server Mail settings, I have "Authenticate Using" set to "Local Users" (which checks the "Digest (CRAM-MD5)" and "Digest-MD5" boxes).


On the client, in the Mail IMAP settings for the account I have selected (picking what I think will be relevant) "Automatically detect and maintain account settings", "Port: 993", "Use SSL", "Authentication: Password" and "Use IDLE command if server supports it". I have NOT selected "Allow insecure authentication". I have previously selected "Authenticaion: MD5 Challenge-Response", but it seems to revert to "Password". I have an iPad and iPhone, both of which have "MD5 Challenge-Response" set, and don't appear to generate anything in mail-err.log


Mail from the Yosemite client works, it is just a bit sluggish. Under Mavericks new messages seemed to arrive simultaneously on all three clients, but now they hit iOS first.

Posted on Nov 6, 2014 3:24 AM

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Posted on Nov 6, 2014 9:19 AM

OK, I think I have solved this. In the client Mail app I de-selected "Automatically detect and maintain account settings". Login then failed. Authentication had switched itself to "Password" while automatic detection of account settings was on. I changed authentication back to "MD5 Challenge-Response", and login now works, I don't get "Authenticating" hanging around in the activity window, and I don't get lots of "authentication failed" messages in the mail logs on the server.

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Question marked as Top-ranking reply

Nov 6, 2014 9:19 AM in response to jilbert

OK, I think I have solved this. In the client Mail app I de-selected "Automatically detect and maintain account settings". Login then failed. Authentication had switched itself to "Password" while automatic detection of account settings was on. I changed authentication back to "MD5 Challenge-Response", and login now works, I don't get "Authenticating" hanging around in the activity window, and I don't get lots of "authentication failed" messages in the mail logs on the server.

Mail slow authenticating to Yosemite server

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