Apple mail and google 2 factor authentication

Question

Level 1

80 points

Apple mail and google 2 factor authentication

I am using 2 factor authentication to connect with gmail. I receive messages without a problem, but when I try to send mail I frequently get a cannot connect error asking for the password to be re-entered. I will then get a new application specific password for gmail and replace the SMTP password. That will work for a day or two, but then it will again fail for sending messages.

Does anyone know if there are particular problems using 2 factor authentication with gmail and OSX mountain lion mail> Am I missing some setting?

thanks for any insights.

MacBook Pro with Retina display, OS X Mountain Lion (10.8.1)

Posted on Apr 18, 2013 11:26 AM

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Answer 1

Eric Root

Level 10

685,257 points

Apr 18, 2013 12:59 PM in response to waldhaus1

Try looking/posting here:

Gmail Support

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Answer 2

waldhaus1 Author

Level 1

80 points

Apr 20, 2013 3:33 PM in response to Eric Root

I had looked there several times - and it didn't specifically discuss 2 factor authentication - that is why I posted my question. I had followed instructions and continued with problems.

Yesterday there was a Macworld article posted online about gmail imap. One thing mentioned in the article that is in addition to what is on the google site is that under system preferences there is a mail contacts panel where the gmail password can also be entered.

I generated a new app specific password and entered it in all three places (sys pref panel, imap server, and smtp server.)

At this time that seems to be working.

Will have to see if it sticks.

Google also had a help item suggesting that if the ask for password dialog pops up when attempting to send mail then get a new app specific password and enter it into that box.

Hopefully the issue is resolved. will give it a few days to be sure.

Thanks

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Answer 3

SStill

Level 1

24 points

Aug 17, 2013 12:04 AM in response to waldhaus1

Many thanks for this - has been driving me crazy.

Really not obvious that there is a third place you need to enter your password now.

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Answer 4

Ladbroke

Level 1

0 points

Jan 11, 2014 9:10 AM in response to waldhaus1

BLUF: The original App-Specific PW was for the incoming mail server (POP3 or IMAP). You need a new one for sending mail.

Just to make the solution a little more explicit:

Go to Mail>Accounts and under Outgoing Mail Server (SMTP) select "Edit SMTP Server List..." from the drop down. From there, go to the Advanced tab. The authentication should be set to Password. From there, enter your new Application Specific password from Google.

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Answer 5

Apr 19, 2014 8:27 AM in response to Ladbroke

Thank goodness!! Now why doesn't Google tell us this?? Btw problems sending through Exchange and problems sending through gmail (both solved now thanks to different users posting on these two very different problems with with identical symptoms), it is a wonder that after about 15yrs of using it, I am still sticking with Apple Mail

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Answer 6

Eric Root

Level 10

685,257 points

Apr 21, 2014 1:14 PM in response to Ebbinghaus

Send Apple feedback. They won't answer, but at least will know there is a problem. If enough people send feedback, it may get the problem solved sooner.

Mail/Provide Mail Feedback

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Answer 7

Jun 28, 2014 7:00 PM in response to waldhaus1

Thanks for posting the solution to this problem. This solved my problem too!

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