Currently Being ModeratedJun 18, 2011 4:57 PM (in response to Steve Darden)
I seem to be having the exact same problem. Did you ever find a resolution to this issue?
Currently Being ModeratedJun 18, 2011 6:11 PM (in response to jmegawarne)
I wish I had a solution for you. I'm using my own domain SMTP since I can't get Google to work.
Currently Being ModeratedJun 18, 2011 6:54 PM (in response to Steve Darden)
I think I may have a solution for you that just worked for me.
- Delete the smtp.gmail.com entry in your Keychain corresponding to the problematic server.
- Revoke and regenerate the application-specific password in Google Accounts. Write it down somewhere too.
- In Mail.app, change the password for the SMTP server to the newly generated one.
- Try to send something. It will probably hang around in Outbox and spin. Leave it there.
- After some time, Mail will prompt you for the password again. Type in the app-specific password and save to your keychain.
- Enjoy working Mail.
I would be interested to know if this works for you. Good luck!
Currently Being ModeratedJun 18, 2011 7:03 PM (in response to jmegawarne)
Very interesting - thanks! Rather weird Mail.app behaviour (delayed login fault).
I can' test right now as (1) we are heading off for a few days and (2) I disabled 2-Step while troubleshooting this SMTP fault. It's a waste of time to reactive 2-step until we get to the next country (USA) and get new mobile numbers.
Soon as we have new mobile I will reenable 2-step and report back here.
Currently Being ModeratedJun 20, 2011 2:59 AM (in response to Steve Darden)
I also found that it helped to force the port to 587 in the SMTP server list.
Currently Being ModeratedAug 19, 2011 1:05 AM (in response to jmegawarne)
Yes, this is mandatory 7th step. I followed the 6 steps above and nothing happend. Manually changing SMTP port to 587 solves this issue.
Currently Being ModeratedDec 5, 2012 12:43 AM (in response to Steve Darden)
Important note you need to create two application-specific passwords. One for IMAP and one for SMTP
Currently Being ModeratedNov 5, 2013 10:57 AM (in response to Steve Darden)
I also had a problem configuring a Gmail POP account in Mail.app. I solved it by using TWO different application specific passwords, one for the POP server and one for the SMTP server.
Currently Being ModeratedFeb 16, 2014 2:48 PM (in response to Steve Darden)
For me, this problem occurs only with Google Apps accounts - these are the ones where you use your own domain e.g. yourdomain.com and not gmail.com.
Wwo-step authentication is disabled on the Google Apps account.
Right click on your mail account name (under Inbox) and click "Edit Account"
Edit the SMTP server list and select the advanced tab.
By default Apple mail only has your user name in the user name field (e.g. user1)
Change this to firstname.lastname@example.org and reenter your password.
I also set the SMTP port to 587
Everything is working fine now