Email alerts stopped working

Thanks Flyvert - that's exactly where it was! Looking at the log I got the below message:

Aug 29 00:16:34 host=smtp.gmail.com tls=on auth=on user=MyEmail from=MyEmail recipients=MyEmail smtpstatus=535 smtpmsg='535-5.7.1 Username and Password not accepted. Learn more at\n535 5.7.1 http://support.google.com/mail/bin/answer.py?answer=14257 xk2sm10987699vec.13' errormsg='authentication failed (GNU SASL, method PLAIN)' exitcode=EX_NOPERM

Looking at the suggested page (thanks Google!) it basically says to double check your login and password. But it also had a little note about if you have 2-factor authentication turned on to check out this page: http://support.google.com/accounts/bin/answer.py?hl=en&answer=185833. Essentially you just need to set up an application specific password. Once I did that and entered that new password into the settings it worked like a charm.

Also of note is the error I got from Yahoo which was:

Sep 08 22:05:18 host=smtp.mail.yahoo.com tls=on auth=on user=MyEmail from=MyEmail recipients=MyEmail errormsg='TLS handshake failed: error:140770FC:SSL routines:SSL23_GET_SERVER_HELLO:unknown protocol' exitcode=EX_IOERR

I'm guessing I would need to turn off TLS for this to work but since Gmail is my preferred method, I didn't look to diagnose that issue.

Thanks