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SBS2008 - Can't connect via terminal services gateway

Posted on 2011-09-28
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Last Modified: 2012-05-12
I am having strange issues with connecting through a TS gateway running on Small Business Server 2008.

I do have a trusted SSL certificate installed on the server.
If i try to connect it rejects valid credentials saying the login attempt failed.
However nothing shows up on the server log for the TS gateway under event viewer.

The same thing happens when trying to sign on via Remote Web Workplace as well, i can sign on to RWW fine but if i try to connect to a computer or the server it rejects the same credentials that worked to sign on to RWW.

It was working at one point in the past and randomly stopped working.

Any ideas?

thank you.
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Question by:jspaziano
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jspaziano earned 0 total points
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I figured it out.

If you ever encounter this, open an exchange management shell and run:

Get-OutlookAnywhere

Check the value of IISAuthenticationMethods, it should read basic, ntlm

in my case ntlm was missing

to correct, run:  Get-OutlookAnywhere | Set-OutlookAnywhere –IISAuthenticationMethods: Basic, ntlm


It can take up to 15 minutes for the change to take effect, you do not need to restart any services.

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