SSTP (SSL VPN) on SBS 2008 RC0

Posted on Posted in 2008, iis, rras, sbs 2008, sstp, vpn, windows

Updated 31st March 2008: Please see http://c7solutions.com/blog/2009/03/configuring-sstp-vpn-on-small-business_31.aspx as this new article replaces the below, as the below refers to a pre-release version of SBS 2008. The working instructions for configuring SSTP on SBS 2008 is much more complicated than the steps below.

SSL based VPN’s are great. In short it is VPN without firewall or NAT issues (both of which you get with PPTP and IPSec VPN’s). But the current release of SBS 2008 (RC0) does not enable SSTP VPN’s by default. It uses RRAS, so SSTP is possible, but it is not as easy as it first looks!

  1. Ensure that you have run the connecting to the internet wizard, and that you are using a third party certificate (as there are less steps if you do this).
  2. Enable remote access from the SBS Console > Network > Connectivity page.
  3. Add some SSTP ports to the VPN in the Routing And Remote Access management program. Right-click Ports and choose Properties and enable SSTP for remote access inbound connections. Leave PPTP enabled as Windows XP does not support SSTP VPN tunnels (only Vista SP1 does at this time).
  4. View the properties of your certificate and note down the Thumbprint value.
  5. Ensure that this certificate is associated with 0.0.0.0:443 and [::]:443: certificate bindings on the server. Type “netsh http show ssl” from elevated command prompt to get this information. You typically get four entries with IP:port being the first line of each. Check for IP:port reading “0.0.0.0:443” and [::]:443 as this shows the IPv4
    and IPv6 mappings for SSL certificates on the server. Ignore the :8172 and :987 entries (these are for IIS Management Service and companyweb).
  6. For both “0.0.0.0:443” and [::]:443 make a note of the Certificate Hash. It needs to be the same for both and the same as the earlier Thumbprint value (ignore any spaces).If not see
    http://blogs.technet.com/rrasblog/archive/2007/11/08/configuring-iis-on-the-sstp-server-implications-and-how-to-resolve.aspx for instructions on resetting this, noting that you need to ensure that the correct certificate is bound to the SBS Web Applications website on the SBS 2008 server (in IIS manager).
  7. Install the “Certificate Authority Web Enrollment” role service to Active Directory Certificate Services snapin within Server Manager. This adds a virtual directory to the default website in IIS called CertEnroll which contains the certificate revocation list for the certificate you are using. Only do this if you are using the built in default issued certificate. If you are using certificates from a third party then you need to ensure you can reach
    their CRL publishing site without issue – see the certificate details for information on the CRL publishing site location.
  8. Expand the Certificate Authority on your server and right-click Revocated Certificates. Under tasks choose Publish. This updates the CRL with the new publishing location that SSTP needs to connected to. Again, use a third party certificate to make this easy!
  9. On a Vista SP1 client create a new VPN connection and in properties > networking ensure that the Type of VPN is set to SSTP (for normal use set this to Auto, and it will find the best (starting with PPTP), but for testing set it specifically to SSTP). Also ensure that the name of the server you are connecting to is the same name that the certificate uses for the certificate common name.
  10. Connect the VPN and all should work.

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