IPSEC Phase 2 address configuration causing SSL

  • Hi folks.

    Perhaps this can help someone, or someone can explain what's going on here.

    Problem Summary
    I have found a scenario where I get SSL certificate handshake errors when connecting to a webserver over VPN between two pfSense servers.
    However, other traffic traverses the VPN without any error. This includes http and ICMP packets.

    Solution found
    The solution was eventually found to be the Phase 2 tunnel definition.
    With the Local and Remote Network types defined on both peers as "Address" with the IP of the test and target servers, the SSL handshake never succeeds.
    Change one or more of the Local and Remote Network types to "Network" with the same IP and /32, and everything works correctly.

    Is this normal behaviour, a bug, or a feature ( :-) ) or is there something I may have misunderstood or did wrong?
    I have not seen this while configuring quite a few Cisco and pfSense VPNs.

    I'll post more details shortly. I'm told the full message is Spam >-)


  • More details are in the attached file. I cannot seem to add it here, because it's supposed spam.
    A little frustrating.