Advice and info request: Squidguard reverse proxy with LDAP and Letsencrypt

  • I'm in need of a reverse proxy that hits the criteria below, can this be done with Squid/Squidgard? Is squid easy to work with on pfSense or should I just look into putting it on it's own VM, ie; would pfSense just be an unnecessary complication here?

    • Three internal web servers serving up http unencrypted, reverse proxy needs to add encryption.

    • Reverse proxy needs to be able to detect namespace:,, and send that to the right internal server

    • Preferred to use Letsencrypt certs, but not required.

    • LDAP authentication before any access is granted.

    I'm currently doing everything except LDAP in Nginx on an Ubuntu VM, thing is I looked at Nginx LDAP and it's just over my head so I'm looking around to see what else is available.

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