Outlook 2011 for Mac prompts for exchange password

[guest]

We are having an issue with Outlook 2011 for Mac clients connecting to our Exchange 2010 SP1 server.
the server settings are configured properly, after launching outlook 2011 for Mac, the initial sync seems to work fine. However, after 2 minutes or so Outlook 2011 asks to allow the autodiscover URI to configure the account. After this it asks for the username and password. We are 100% sure that we have correct credentials. The following log entries show up in the troubleshooting log.

[ 2403us, d 584us] Outlook Exchange Auto Configure: Querying https://cas.domain.name/autodiscover/autodiscover.xml
[ 2432us, d 29us] Outlook Exchange Auto Configure: HTTP send message failed with error code: 401
[ 2432us, d 0us] Outlook Exchange Auto Configure: === Failed to retrieve autodiscover settings for user@domain.name

My first thought is that this was an authentication method issue. Here is the results of our autodiscover virtual directory config query:

RunspaceId : 8cb0da41-c4fc-4f36-aafa-e46bc9fb60ca
Name : Autodiscover (Default Web Site)
InternalAuthenticationMethods : {Basic, Ntlm, Digest, WindowsIntegrated, WSSecurity}
ExternalAuthenticationMethods : {Basic, Ntlm, Digest, WindowsIntegrated, WSSecurity}
LiveIdSpNegoAuthentication : False
WSSecurityAuthentication : True
LiveIdBasicAuthentication : False
BasicAuthentication : True
DigestAuthentication : True
WindowsAuthentication : True
MetabasePath : IIS://mbx.domain.name/W3SVC/1/ROOT/Autodiscover
Path : C:\Program Files\Microsoft\Exchange Server\V14\ClientAccess\Autodiscover
ExtendedProtectionTokenChecking : None
ExtendedProtectionFlags : {}
ExtendedProtectionSPNList : {}
Server : MAIL
InternalUrl : https://cas.domain.name/autodiscover/
ExternalUrl : https://cas.domain.name/autodiscover/
AdminDisplayName :
ExchangeVersion : 0.10 (14.0.100.0)

Note that I've obviscated server and URLs for security reasons. However SSL certificates are installed at the appropriate endpoints.

Note that this same user is able to be confirmed as working by the microsoft exchange connectivity test tool. With settings discovered using autodiscover. Windows Outlook 2007 and 2010 clients work flawlessly with this same account.

Anyone have any idea what might be causing this?

Any help would be appreciated.

[guest]

Do all Mac clients have the issue?

Do you have legacy Exchange in the organization?

Please try to reset the EWS Virtual Directory to test.

Server Configuration->Client Access->Actions->Reset Virtual Directory->Browse->EWS


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[guest]

Resetting the EWS and autodiscover directories did the trick after re-adding the external and internal URLS. Thanks for the pointers!