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I have squid-deb-proxy working fine without a problem without apt proxy authentication. However when I add a proxy file to /etc/apt/apt.conf.d and put in my proxy authentication inside this file. Running sudo apt-get update does not work it misses the update and ignores.

However when I move out or comment the file that squid-deb-proxy-client created inside /etc/apt/apt.conf.d which is 30autoproxy and contains 1 line pointing to /usr/share/squid-deb-proxy-client/apt-avahi-discover the APT-GET update works without a problem.

Note that observing the logs of /var/log/squid-deb-proxy/access.log does not log any successful entry. Going without proxy logs successful entries and apt-get update works.

So bottom line how to make squid-deb-proxy-client on the main ubuntu machine to work thru proxy that has authentication.

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I am a little confused by your question. Is your squid-deb-proxy server behind a proxy which needs authentication? Or do you want you squid-deb-proxy clients to authenticate against the squid-deb-proxy server?

In the former case, I put cache_peer proxy.acme.corp parent 8080 0 no-query default login=username:password in /etc/squid-deb-proxy/squid-deb-proxy.conf.

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