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.

How to add your school gmail account to Outlook 2011 for the Mac. First you need to make sure that you have the latest version of Microsoft Outlook 2011 for Mac installed. You can find more information about how to update in the first step in this guide. Next, click on Tools in the top menu and then click on Accounts.

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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 x19sm5358056qeq.12 Cannot send mail.

The SMTP server does not recognize any of the authentication methods supported by Outlook. Google chrome 8 for mac 10.6.8. 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.