Multiple proxy servers on one pfsense box

  • I am wondering if it is possible to have two proxy servers on the same pfsense installation. I want to setup a proxy that the majority of machines are routed through (these will be computers in classrooms). I then want teachers to authenticate against a different proxy on the same pfsense box so that I can have different content filtering. Is this possible, or is there a different way I can achieve this?

    I don't want the classroom machines to have to authenticate with the proxy, only anyone wanting to access the teacher proxy?

  • Why not setting up another small Squid Proxy outside of the pfSense appliance?

  • Thanks for your reply. Yep I could do that but wanted to try and keep it to a single box, and thought there might be a more elegant solution. But if a second box is the way to go I will give that a try.

  • You can install Dansguardian, which can be used in conjunction with Squid Proxy to transparently authenticate via Windows Active Directory. You can then set Dansguardian to assign different proxy policies dependent on which Windows AD groups the user belongs to. I've done this using Dansguardian/Squid on a separate proxy system, although I believe this is also possible using the same Dans/Squid combination on pfSense itself. If your teachers and students are all using Windows logins, then this might be the more elegant way forward.

    I've found this link pointing back to this forum about two years ago. It might help point you in the right direction:

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