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How to set up Windows Server 2008 certificate server for Cisco AnyConnect VPN authentication

Posted on 2014-11-01
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Last Modified: 2015-02-11
I am tasked with an immediate need to configure a windows server that can serve as a CA such that I can use it to generate certificates that can be deployed to VPN-enabled computers by Group Policy to serve as a second means of authentication on top of a username and password.

My Cisco AnyConnect VPN is served up from a Cisco ASA 5515 firewall with latest and greatest firmware (9.2(2)8). I installed an SSL certificate from GoDaddy, so that the ASA is identified as a trusted VPN connection. But, I'm under the impression that VPN clients need a certificate on the native machine in order to provide a second form of authentication and that the SSL certificate on the ASA identifying it as a trusted VPN connection does not actually serve as a valid 'factor' in multi-factor authentication terms.

In the end, my VPN connection needs a second factor of authentication on top of the first factor (RADIUS).  I'm, again, under the impression I need to go down the road of an internal server as a CA.  However, I have done zero work with certificates and certificate servers in this capacity and it's all new to me.  Given that I have the GoDaddy SSL cert on the ASA, I wonder if there is a way to leverage that.

Reading up on it, I'm finding myself questioning whether I need a standalone CA vs an enterprise CA, if I can install it on a domain controller or if it should be installed on a member server, how the certificate generation and deployment process to VPN clients (Group Policy) all comes together.

Hopefully having described my situation, what I'm working with, what I need to accomplish in some form or another, and what I'm specifically trying to vet out will help someone help provide me some direction.
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Question by:djhath
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Pete Long earned 500 total points
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by:djhath
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Thanks, Pete.  I came across your article last night and had it separately bookmarked.  I started digging into your approach and trying to adapt it to the leverage the existing GoDaddy CA certificate and corresponding Identity certificate installed on the ASA.  However, what I forgot to mention was that I have a failover pair and the ASA cannot be set-up as a CA server when failover is enabled.
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by:Pete Long
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Ah ok in that case id setup a CA on a windows server, import the CA cert onto the ASA as a trusted authority, then issue 'computer certificates' to the remote machines.
Deploying Certificates via 'Auto Enrollment'

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by:djhath
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Thanks, Pete. I will give that a shot and report back.
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by:djhath
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You have been a tremendous help. I have deployed the certificates as your article depicts. I am going to adjust my RADIUS configuration and test authentication with the certificate.
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by:djhath
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Much closer, but not quite there yet.  I have successfully exported and imported the Windows domain CA certificate into the ASA.  To test, I have set the authentication mechanism to Certificate from AAA. When I attempt to connect with the AnyConnect client, it prompts with the machine's certificate , which I am supposed to select for authentication. I select it, and responds back with 'Certificate Validation Failure'.
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by:Pete Long
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Does the remote computer have a certificate issued from your PKI on it?
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