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    OpenVPN site-to-site server certificate verification failing when using an external PKI

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    • T
      Tactis
      last edited by

      I've run into an issue trying to configure peer-to-peer (SSL/TLS) when using pfSense as a subordinate CA to an ADCS (Active Directory) CA.
      Are there any caveats or reasons why using an external root CA doesn't work in this scenario?

      • ADCS CA is created
      • ADCS creates a subordinate CA, the CA cert & key imported into pfSense at site A.
      • Site A created a server cert signed by the above CA and uses it on an OpenVPN peer server.

      When trying to connect, the client pfsense at site B always fails to connect with TLS Authenticatino Error. From the logs:

      VERIFY ERROR: depth=1, error=self signed certificate in certificate chain: C=…
      OpenSSL: error:14090086:SSL routines:ssl3_get_server_certificate:certificate verify failed 
      

      The issue seems to be the same with any of the processes below:

      • Site B imports the ADCS CA and pfsense subordinate CA from site A seperately
      • Site B imports the ADCS CA and pfsense subordinate CA as a chain
      • A user cert(signed by the CA) is generated in site A and exported and imported into site B.
      • A CSR for user cert is generated on site B and signed by site A
      • The tunnel uses the ADCS CA as the peer certificate authority
      • The tunnel uses the pfSense subordinate CA as the peer cert authority.

      I instead exported the internal self-signed CA from site A, create a user cert and imported the CA and Cert into site B and it works. After some searching it seems that others have had the same issue.

      This is the guide I've been using, I have a lot of experience already configuring shared key site tunnels and OpenVPN remote access servers, just Peer & PKI is new to me.
      https://docs.netgate.com/pfsense/en/latest/vpn/openvpn/configuring-a-site-to-site-pki-ssl-openvpn-instance.html

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