VPN Pivoting

  • Hello all,

    I'm trying to do VPN pivoting using PfSense along with OpenVPN so I can use tools "like" zenmap to scan the VPN client's remote sub-net.  I read that its possible using iroutes and push, but have not been able to do more than the client machine, after going through several write-up's and trying to make-sense of the fragmented answers, I've been spinning my wheels.

    My goal is as follows;

    • support windows, OS-X, and Linux devices to do remote VPN pivoting
    • minimize the configuration needed if/when a different sub-net needs to be scanned (not having to manually edit the config for a different sub-net)
    • use the most ideal way to use windows-based scanner's to point towards the VPN tunnel (in hopes to avoid same sub-net as host.)
    • be scalable.

    I was thinking that ideally there would be 3 parts to this; the windows box (scanner resides) that uses VPN client to connect the PfSense VPN server (remote/local), then another VPN client on a remote network, where one can scan its sub-net)

    I'm all ears, and really need a solution quickly! if a financial gain is a motivator for you to help me with my goals, We can work something out.  ;)

  • bump

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