Transparent web filtering https+http proxy to clarify

[vielfede]

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 https://forum.pfsense.org/index.php?topic=112335.0

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