Windows Server 2008 SSL VPN (SSTP)

Now-a-days, every business is mobile, which means a VPN connection is most likely needed.  The problem is when clients travel to hotels or other countries, where firewall compatiblity and configuration can cause connectivity issues.  Fortunately, there is an answer for this: SSL VPNs.  Since an SSL VPN connection is secure and allowed on almost all firewalls, remote users will have a much more reliable connection mechanism; no matter where they are.  To top it off, SSL VPN (SSTP) is a feature natively bundled with Windows Server 2008.  How cool is that?

How does SSL VPNs help?

  • A NAT device doesn’t need to support PPTP in order for it to work.
  • Specific ports aren’t required to be open on the firewall (think hotels and other countries).
  • Connectivity can be made through web proxy servers.
  • The small footprint VPN client is easily accessible.

Clients supported: Vista SP1+, Windows 7, Windows Server 2008

What are the high level steps involved to setting up Windows Server 2008 SSL VPN connections (SSTP)?

  • Obtain a certificate to be used for your connections (just as if you are installing an SSL certificate for your website)
  • Install IIS on the VPN server
  • Request a certificate for the VPN server using the IIS Certificate Request Wizard
  • Install the SSL certificate
  • Install the RRAS server role on the VPN server
  • Enable the RRAS Server and configure it to be a VPN server
  • Configure the User Account to allow dial-up connections
  • Update DNS (ie.
  • Configure the Client to use SSTP and Connect to the VPN Server using SSTP

How-To configure Windows 2008 for SSTP VPN
1.  Install IIS on VPN server with all security settings marked for installation
2.  Create a Certificate Request in IIS console
a.  Make sure common name is actual Internet Hostname clients will connect to (e.g.
3.  Cut and Paste the certificate request into your SSL provider’s website
4.  Install any Intermediary certificates and your SSL certificate per your SSL provider’s instructions (DO NOT bind the certificate to a website in IIS)
5.  Install Routing and Remote Access
6.  Load the Routing and Remote Access MMC and run the wizard to enable it (Select Custom -> VPN if you are using only 1 NIC)
8.  Enable Dial-In access for the remote user’s AD account
9.  Enabled SSL connection (port 443) from the outside
10. Update DNS for the domain with the common name of the certificate
11. Test the SSL VPN connection by choosing SSTP in the vpn network connection properties

If the connection doesn’t work, make sure the proper certificate is bound following:
1.  Make sure the right certificate hash is bound (netsh http show  ssl)
a. If necessary, delete and readd the correct certificate binding…
1. Remove binding from IPv4 (netsh http delete ssl
2. Remove binding from IPv6 (netsh http delete ssl [::]:443)
3. Delete registry entry for the hash (reg delete hklmsystemcurrentcontrolsetservicessstpsvcparameters /v sha256certificatehash /f)
4. Add binding from IPv4 (netsh http add sslcert ipport= certhash=<replace with your cert hash> appid={ba195980-cd49-458b-9e23-c84ee0adcd75} certstorename=MY)
5. Add binding from IPv6 (netsh http add sslcert ipport=[::]:443 certhash=<replace with your cert hash> appid={ba195980-cd49-458b-9e23-c84ee0adcd75} certstorename=MY)

Helpful links to configuring SSTP VPN:

  • A step-by-step guide to setting up your own SSTP server is to be found here.
  • Troubleshooting help can be found here, here, and here.