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Remote Desktop certificate update problems

Posted on 2014-08-13
Medium Priority
Last Modified: 2014-08-23
I recently updated the certificate on my server hosting IIS7 and Remote Desktop Services.  The new certificate is installed under the MMC and bindings set in IIS.  The certificate was also set in Remote Desktop Gateway Services.  However, connecting to the HTTPS interface on the server still shows the old expired certificate.

Need some help running this down.
Question by:chronolith
  • 4

Expert Comment

by:Chad Franks
ID: 40258227
How did you import the new cert?  into the machine/personal store? via the MMC or just point to it from IIS?  Did you physically delete the old cert?

Author Comment

ID: 40262994
I imported first through the MMC and then into IIS in accordance with GoDaddy's instructions (who issued the cert).  I did not physically delete the old cert.  Is this done through the MMC or do I need to go and sniper the file?

Author Comment

ID: 40263143
Found some old certs on my proxy server.  Deleted them and installed the new one in the MMC.  No change.

Accepted Solution

chronolith earned 0 total points
ID: 40268571
OK figured it out myself.

Setup is IIS7 on windows 2008.  Installed the cert using GoDaddy instructions.  Reset the bindings to use the new cert in IIS.  Updated the RDS gateway to use the new cert also.  Exported the cert as a PFX file from MMC including private key and all the details.  Imported the certificate to my Forefront TMG and set the web listener to use the new cert.

Never used Forefront before and turns out it was the problem the entire time.  Lesson learned.

Author Closing Comment

ID: 40280284
Figured it out myself.

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