Chrome for Business and SQUID Proxy - Secure Connection?

epionier

Hello,

I use pfsense on the local network running SQUID on 10.21.30.1 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:

I used GPO for manual proxy connection and entered 10.21.30.1:3128 because https://10.21.301.1:3128 is not working
(Which should be possible according to:http://dev.chromium.org/developers/design-documents/secure-web-proxy)
In chrome it asks then for proxy authentification. This is working but this is a unsecure connection because in the authentification it says http://10.21.30.1:3128 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?
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.