PFSense stuck behind squid proxy

  • Hi Everyone

    I did have a look and did not find this specific issue on the forum … If it is, please let me know :)

    I am using PFSense 2.0.1. I have configured squid as a proxy as I want to eventually enable transparent proxying for my users.
    The configuration I have to work with is as follows:

    Internet <---> Proxy A <---> PFSense Box <---> Users Set 1
                                | ---> Users Set 2

    The only way anyone can access the internet is through Proxy A and it only accepts requests on port 80 and 443. Other than this, there is no other internet access. Email is handled by a separate internal mail relay which has it's own internet access. For this reason the PFsense Box is configured with an upstream proxy which allows it to update and download packages.

    Now, my problem:
    When I configure proxy access (without enabling Transparent Proxying), access through port 80 works quite fine. HTTPS access, however, does not work. Now, I know that squid does not proxy HTTPS traffic. I think my problem has something to do with the routing on the box - possibly that HTTPS is not being routed to the correct address (Proxy A)?

    Any help would be appreciated!


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