Chrome for Business and SQUID Proxy - Secure Connection?

  • Hello,

    I use pfsense on the local network running SQUID on with local authentification.

    I downloaded Chrome for Business that allows me to configure settings via (ADM / GPO).

    Unfortunately I am unable to get Chrome working with SQUID properly with a secure connection.

    I want that Chrome connects to the squid server with a secure connection (TLS) no matter if the destination website ist HTTPS or HTTP.

    What I have done:

    1. I used GPO for manual proxy connection and entered because https://10.21.301.1:3128 is not working
      (Which should be possible according to:
      In chrome it asks then for proxy authentification. This is working but this is a unsecure connection because in the authentification it says and not https.//…...
      How do I switch to TLS connection?
      After importing the local certificate of SQUID I am able to connect to HTTPS sites. But is the connection to the local SQUID server then secure with TLS?

    2. By the way, does anyone know a possibility that Chrome does not ask for proxy authentification on startup? I get the prompt every time I open Chrome no matter if the credentials are saved or not.

    I know this a certain question for Chrome but it depends on SQUID, too.
    Maybe someone can help me out.

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