Outlook 2011 will not accept Exchange credentials

I have a problem with one of our Macs using Outlook 2011. When I try to add an exchange account it picks up the CNAME record and pulls down the settings for the account but keeps saying "Mail could not be received at this time" Logon failure unknown user or bad password, Your username/password or security settings may be incorrect.

I can log in to OWA with the same credentials just fine and add the account elsewhere without a problem it just fails on this Mac


Mac OSX Yosemite 10.10.1
Outlook 2011
Microsoft Exchange 2013

Any help would be most appreciated.

I have tried:

Using keychain first aid
Uninstalling and reinstalling Office 2011
Resetting users password to a different password
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David AtkinTechnical DirectorCommented:
Have you tried defining the domain with the username?


Can you give us a screen shot of your Outlook Anywhere settings?
purpleoakAuthor Commented:
We have tried DOMAIN\USERNAME instead of e-mail address but still get the same error message.
David AtkinTechnical DirectorCommented:
It will want to be the persons username and password, not the email address - In most cases anyway.

Can you tell us what settings are in Outlook Anywhere please?

Try changing the proxy authentication settings to 'basic authentication'
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purpleoakAuthor Commented:
server settings
Delegates settings
Security settings
In IIS on your CAS server(s), can you check your EWS directory's authentication settings and make sure you have Basic auth selected. If not then select it and apply. Then do an 'iisreset /noforce' on you CAS server(s). If the '/noforce' option doesn't it work take it out and try again. Then launch Outlook on your MAC again.
purpleoakAuthor Commented:
Does not seem to have made a difference, One thing to add which I have just discovered is that the SSL certificate for the domain on this server was renewed last Wednesday and updated on the server using the same provider and type of certificate as before.
purpleoakAuthor Commented:
Problem solved by completely removing Office 2011 and all associated licenses and files and then reinstalling Office 2011 and installing all available updates.

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purpleoakAuthor Commented:
This solution solved our problem
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