PFSense Squid + Squidguard Web Filter Help

  • I'm hoping this topic hasn't already been covered, if it has I apologize. I've been plugging away trying to get a PFSense box with squid and squidguard filtering content for about 3 weeks. I did have in functioning at one point, but the hardware I was using was simply for testing purposes. Now I cannot seem to get the proxy and filter to function using the settings I had created from the previous test. The following is the problem:

    • I cannot ping the WAN Interface, and therefore the box itself.

    • The connection works on the test computer, but once I set the gateway to the PFSense box, it times out meaning there is a communication issue in PFSense.

    • The PFSense does have the gateway and DNS servers set, and squid is set to run as a transparent proxy.

    We are running this in a virtual environment now, however I have tested it on another spare system and I am having the same issue. We were hoping to run this on one interface, as the server will be added to an existing network with other servers with IP addresses and DHCP already configured. However I have a feeling that the single WAN interface coupled with the firewall may be the issue.

    That aside, the other issue I had when it was working was with the block page. Any time I tried to customize the page and add my own images, the PFSense box refused to pull the images from the box itself or from another server. I tried a number of options I found from searching and none seemed to help. I'm hoping some members on here who have set this up and customized pages can help me out, I've been working on this for some time and would like to get it functioning.

    If you need further info I will be happy to provide it, I can also take screenshots as necessary.

  • Using non transparente proxy, you can have squid on one network card pfsense.

    To ping, you need to create a firewall rule for it.

    transparent proxy is not able to filter ssl, so It's better to configure proxy.pac/wpad.

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