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Outlook 2007 failing to authenticate with Outlook Anywhere.  RPC over HTTP

Posted on 2009-04-27
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I have a new exchange server 2007, everything working but Outlook Anywhere.  Basically Outlook just prompts for username and password over and over again.. as if i am entering it wrong.. I am not :)

Server config:
I have port 443 forwarding to my interior exchange server.
testexchangeconnectivity.com just reports a certificate error, dns and 443 connect
Server is installed and configured to enable outlook anywhere on mail.mydomain.org basic authentication
iis7 shows rcp and rcp with cert web sites
certificate is self signed mail.mydomain.org

Outlook Config
My Certificate is installed Trusted Root Certificate Authorities
https://mail.mydomain.org
mssdt://mail.mydomain.org
basic authentication
username and password same as i log into owa  

Anything i am missing.. Some permission for the user to connect somewhere.. maybe a setting in the UO group or a setting in iis 7 to allow rcp.. I have to be missing something.
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Question by:brandonjel
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Expert Comment

by:Mestha
ID: 24244931
If the test site is reporting a certificate error, then that is a problem, as certificate errors are a hard failure for this feature.

Browse to https://host.example.com/rpc from the machine and see what happens. You should only get an authentication prompt - which will fail, that is to be expected.

Which authentication method do you have enabled in Exchange 2007? Basic or integrated?

Simon.
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Expert Comment

by:Narayan_singh
ID: 24244933
Go throught the aticle below:
Deploying Outlook Anywhere
http://technet.microsoft.com/en-us/library/aa998934.aspx
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Expert Comment

by:ikshf143
ID: 24244951
Hi,

First from an internal client try to browse https://mail.mydomain.org/rpc/rpcproxy.dll and see what you get. The expected result is a Blank page. Try the same from an External Client. Make sure from external or internal client we should not get any certificate error when we trying to browse https://mail.mydomain.org/owa.

Try to create an Outlook Anywhere profile on an Internal Client and check the connection status to check that after configuring a profile go to Start-->Run and enter Outlook /rpcdiag

Imran
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Accepted Solution

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esmith69 earned 2000 total points
ID: 24244964
I am assuming above where you have "mssdt://mail.mydomain.org" is just a typo?  The correct spelling should be msstd

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