What type of certificate to install on the VPN server

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Hello Friends,

In my previous posting related to VPN tunnel selection, I discussed various scenarios in which you need to install a certificate on the VPN server. To summarize this requirement in a nutshell: except PPTP tunnel, for all the other tunnel types (i.e. IKEv2, SSTP and L2TP/IPSec) VPN server machine should be installed with a valid certificate. And what does valid means is what I am going to discuss in this blog.

Let us take a simple deployment scenario: You have one VPN server which is enabled for all VPN tunnels and is also used as NPS based Radius server – with EAP-TLS authentication.

Here are the steps you need to follow:

1) Install a certificate inside machine store (i.e. Local Computer certificate store) of the VPN server. The key properties that you MUST ensure are set inside the machine certificate includes:

  • Common name (CN): Same as the hostname OR IPv4/v6 address that is configured as VPN destination on the VPN client. i.e. if the VPN client is configured with the hostname, then set this as same hostname OR if the VPN client is configured with the IP address, then set this as same IP address.
  • Extended Key Usage (EKU) :  Select “Server Authentication” and “IP Security IKE intermediate”.
  • Key Usage: Select Digital signature and Key encipherment.

This certificate must be requested from the certificate authority (CA) – who trust chain is installed on the VPN client machine (see next step on special care if you are using public CA). The certificate can be requested from the CA using any mechanism that supports requesting above set of properties. For example, if you are using Active Directory Certificate Services – you can request a certificate by creating a “Custom request” by clicking on relevant certificate store inside Certificate Manager (certmgr.msc). And you can then submit the certificate request to the CA. And once the request is approved, you can install the machine certificate on the VPN Server.

2) Once the certificate is installed on the VPN server, you must configure the VPN server appropriately to point to the relevant machine certificate:

For SSTP: Ensure the SSTP tunnel is configured for this certificate. For Windows 2008 R2 – RRAS server has a UI/netsh way of selecting the certificate that will be used by SSTP – which is blogged here. For Windows 2008, there is a regkey driven way of ensuring the same which is blogged here and here.

For L2TP/IPSec: No other configuration is required

For IKEv2 EAP authentication: No other configuration is required

For IKEv2 machine certificate authentication: Ensure the trusted root certificate store on the VPN Server contains **only** the trust root certificate that matches the trust chain with which the client will send the machine certificate. And you MUST delete all the other trust chain on the VPN Server – to avoid any malicious client machine having a certificate with one of those trust chain to be able to successfully connect to this VPN server using IKEv2 machine certificate authentication. WARNING: If you have enabled IKEv2 machine certificate authentication scenario, you MUST NOT install any trusted root certificates from a public certificate authority (e.g. Verisign) on the VPN server machine. Otherwise, any malicious user  with a machine certificate from that particular public CA – can connect with your VPN server. You must only install the trusted root certificate of your own certificate authority.

Hope this posting helps you select the right certificate

For further details about the certificates, please refer to this excellent blog by Adrian.

With Regards,

Samir Jain

Senior Program Manager

Windows Networking

[This posting is provided "AS IS" with no warranties, and confers no rights.]