Outlook 2010 + Exchange 2010 Outlook Anywhere + TMG2010 + NTLM does not work

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I'm trying to get Outlook 2010 to connect to my Exchange 2010 server using Outlook Anywhere.

Outlook 2007 can connect just fine. It properly runs autodiscover and configures everything. Email just works. NTLM auth is selected for Exchange Proxy.

Outlook 2010, using the same setup, does not connect. It shows the following error:

"The action cannot be completed. The connection to Microsoft Exchange is unavailable. Outlook must be online and connected to complete this action".

TMG shows the following:

"Error: The server requires authorization to fulfill the request. Access to the web server is denied. Contact the server administrator"

If I install Outlook 2007 and create the account settings, and then upgrade to Outlook 2010 it connects to the server just fine.

My setup is:

- Office 2010 Professional Plus on the Client

- Windows 7 Professional

- Exchange 2010 using the latest rollup

- TMG between the client and Exchange 2010

- The certificates are from an internal PKI. The Root CA certificate is properly installed on the Client Trustes Certification Authorities. Internet Explorer does not show any error accessing the exchange pages using https. Outlook 2007 does not complain as well.

I already checked that all URLs from Autodiscover work properly.

No errors are shown on Exchange or TMG.

Any idea what can be the problem?



Hi ricdgr,
It sounds an odd issue.
Per your descriotion, you are testing the outlook 2007 and outlook 2010 from the external domain, and outlook 2010 could not connect to the exchange server successfully, right?
1. What about in your internal domain, you could check the autodiscover service in your internal domain, make a test through outlook 2007 and outlook 2010
2. Could you please make a test from the external domain bypass the TMG
3. Confirm that the account you used to make test is exist and the account name&password correctly
4. Use the NETMON to retrieve the session log to check the issue when you configure the outlook 2010 for special account
And then we could narrow down the issue, we could do more research regarding to your issue.
About the TMG error, you could refer to below for some useful information.



1. Outlook 2010 works fine on internal domain

3. Account exists and password is correct

Will now try to get the answers for 2. and 4.

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