Creating an SSL VPN with Windows Server 2008 R2

This week I was in Las Vegas for the Exchange Connections Conference.  Traveling usually isn’t too much of a hindrance anymore of the availability of a wireless Internet connection just about everywhere you go.  The only downfall is that most public places, particularly hotels, tend to provide Internet access but block non-HTTP traffic in a lot of cases.  For VPN users, this can be a problem and prevent you from accessing the resources that would normal require you to be connected directly to your corporate network.

With Windows 2008, the Routing and Remote Access service can now be used as a means for providing access via VPN to corporate resources.  Since SSL is a common protocol and just as common as it’s HTTP counterpart, it is usually accessible.

I spent a couple of hours tonight working on creating a SSL VPN solution for my network.  I did get it up and running and wanted to provide some of the resources that helped make this process a lot easier. 

The IT Consulting Blog had a good amount of information that got me through some of the pitfalls.

This IT Technology Blog helped a lot when it came to troubleshooting.

I was able to get connected and everything is working great – but – one thing I did have problems with was when the SSTP Client in Windows 7 connects to the VPN Server, it has to make contact with the Certificate Revocation List to check and make sure that the certificate used for the VPN communication hasn’t been revoked.  I am using ISA which may or may not add a layer of complexity, but I did have to disable the CRL check.  At first, I thought the registry edit that disabled that was made on the VPN server, but in fact, it is actually made on the client machine.  You probably don’t want to disable CRL in a production environment – so just keep that in mind.

Microsoft has a section in this article that talks about the registry key required to disable or enable the CRL check.

Finally, Tom Shinder, one of the great ISA experts out there wrote a series on implementing a Windows 2008 VPN behind ISA infrastructure.  This walks you through the entire process from start to finish.  You can find that three part series here.