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and what about a Fully working without bugs squid + ubuntu?
what iso did you found?

i maintains couple squid instances for more then 2 years and authentication seems to work great for me.
if you are having troubles with auth i will be more then happy to assist you in it here or...

you need a "VPN server" with nat and routing capability.
squid i a fine product.
i suppose you have windows client.
so you can use "poptop" as pptp server and use iptables on the remote machine r...