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Having spent a while debugging this, I thought I'd post here so others can save some time.

The error from Outlook 2011 is: "The SMTP server does not recognize any of the authentication methods supported by Outlook. Error code: -17092".

All other modern email clients are able to send and receive email happily, just Outlook 2011.

The issue is around the "250-AUTH PLAIN" response that SMTP gives. Outlook 2011, just like old Outlook versions from 10 years ago require "LOGIN" as well.

The fix for me was to add this line to my dovecot.conf: auth_mechanisms = plain login

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Thanks, we had the same problem. –  kaleissin Mar 15 '13 at 7:01
    
Had the same issue but didn't find this answer till I started writing my own question about it. As you didn't mention the error message 'Authentication failed because Outlook doesn't support any of the available authentication methods' which is what I had been googling for. But anyway thanks a million I'd given up all hope on solving this. –  Mark Davidson Oct 8 '13 at 17:02
    
If you want this to not get closed, you should convert it to ask a question which you then provide an answer to. –  Nigel Nquande Mar 23 at 11:05
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