When “All” isn’t everything you need – Terminal Services Gateway certificates.

Setting up Terminal Services Gateway on Windows Server 2008 the other day.

It’s an excellent technology, and one I’ve been waiting for for some time – after all, it’s fairly logical to want to have one “bounce point” into which you connect, and have your connection request forwarded to the terminal server of your choice. Before this, if you were tied to Terminal Services, you had to deal with the fact that your terminal connection was taking up far more traffic than it should, and that the connection optimisation settings couldn’t reliably tell that your incoming connection was at WAN speeds, rather than LAN speeds.

image But to get TS Gateway working properly, it needs a valid server certificate that matches the name you provide for the gateway, and that certificate needs to be trusted by the client. Not usually a problem, even for a small business operating on the cheap – if you can’t afford a third-party trusted certificate, there are numerous ways to deploy a self-signed certificate so that your client computers will trust it.

I have a handily-created certificate that’s just right for the job.

I ran into a slight problem when I tried to install the certificate, however.


The certificate isn’t there! In this machine, it isn’t even possible for me to “Browse Certificates” to find the certificate I’m looking for. On another machine, the option is present:


That’s promising, but my certificate doesn’t appear in the list of certificates available for browsing:


I checked in the Local Computer’s Personal Certificates store, which is where this certificate should be, and sure enough, on both machines, it’s right there, ready to be used by TSG.


So, why isn’t TSG offering this certificate to me to select? The clue is in the title.

The certificate that doesn’t show up is the one with “Intended purposes: <All>” – the cert that shows up has only “Server Authentication” enabled. Opening the certificate’s properties, I see this:


Simply selecting the radio-button “Enable only the following purposes”, I click “OK”:


And now, back over in the TSG properties, when I Browse Certficates, the Install Certificate dialog shows me exactly the certificates I expected to see:


This isn’t a solution I would have expected, and if that one certificate hadn’t shown up there, I wouldn’t have had the one clue that let me solve this issue.

Hopefully my little story will help someone solve this issue on their system.

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