I am using Mac OS X 10.7.5 and Mac Office 2011 Outlook. I am trying to connect two gmail-based accounts via imap. One account has a gmail domain address. The other is a google apps mail account (i.e. doesn't have a gmail.com address but is powered by gmail).
The gmail account can send/receive with no issues.
The google apps gmail account can receive but cannot send email from Mac Outlook. I get the following error:
5.5.1 http://support.google.com/mail/bin/answer.py?answer=14257 x19sm5358056qeq.12
Cannot send mail. The SMTP server does not recognize any of the authentication methods supported by Outlook. Try changing the SMTP authentication options in Account settings or contact your network administrator.
I've checked the settings of both accounts - they are identical in terms of the outgoing mail server (smtp.gmail.com) with the SSL and to port 465. I've also tried sending email from the google apps mail account via the browser and it works. I've tried this multiple times and it fails consistently.