Another quick one on my journey down the Remote App functionality of Server 2008 TS.  I have set up a few apps in SharePoint and they worked internally, but when accessing them externally they failed with a certificate error.  The error indicated the certificate wasn’t trusted as it was a self generated one, the text of the error was:

Your remote desktop connection failed because the remote computer cannot be authenticated
The remote computer could not be authenticated due to problems with its security certificate.  It may be unsafe to proceed.
Name mismatch
Requested remote computer:
<farm.domain.local>
Name in the certificate from the remote computer
<servername.domain.local>
Certificate errors
The following errors were encountered while validating the remote computer’s certificate:
The server name on the certificate is incorrect.

Now we have a GoDaddy purchased certificate on our SBS server and this Technet article talks about signing RDP files with the cert so they are trusted.  I went through this procedure but unfortunately the same problem remained.  A bit of Googling found this unusual fix in a Technet forum, but it worked.  The only caveat was that I had to remove and re-add the apps from the Remote App list.

1. Open TS Remote App Manager
2. Click ‘Change’ next to ‘RDP Settings’
3. Select the ‘Custom RDP Settings’ tab
4. Add the text ‘authentication level:i:2’ to the Custom RDP Settings dialog
5. Add your Remote Apps and they should now work externally through TS Web

I’d expect the true fix for this would be to change the certificate from the locally generated one to a the purchased one, however I can’t find any reference in Google to this and I can’t find where in TS this cert is being used.  Anyway, it worked and that’s what matters!

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