>I am going to assume that is a problem with it being a transparent proxy?<

Yep. That is another issue to take care of.
Look here: 
http://wiki.squid-cache.org/Features/BumpSslServerFirst

I suggets, first do NOT take SSL into consideration. Adds another layer of
complexity.
First, get your setup running with http only.
Then, a more knowledgable guy has to take over giving you advice.
As you see a lot of postings in the forum dealing with SSL, this is quite a
"famous" issue :-)




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