Transparent web filtering https+http proxy to clarify

  • Hello,
    as it seems to me that there is some confusion about it on that forum section (and in my my mind as well), after I spent a lot of time trying to configure a transparent proxy to allow web filtering, and after some explanations request to the local pfsense support,  I'd like to clarify some facts about it, just to avoid other useless attempt.

    **The goal:**A transparent proxy allowing

    • caching + web filtering for http

    • web filtering for https

    Client configuration: avoided (no proxy settings, wpad, certificate installation on client, etc)
    Packages to use: squid and squidguard

    FACTS (please correct me if I am wrong)

    • That kind of configuration DOES NOT WORK, to be more precise, the https part does not because of some programs connection issues (e.g. Chrome)

    • The most similar working conf is by use of WPAD (documentation here

    Please let me know if my deductions are wrong.

    Moreover, I was no able to understand why the use of wpad is mandatory, if anyone can explain me, I'd appreciate it very much.

    If something should change I promise to update this topic
    Thank you