You are beginning to discover just how bizarre and broken the idea of
a 'transparent' http proxy really is. It's not actually possible to
have a truly transparent one that isn't somehow broken (although it is
sometimes possible to have one that is broken only in ways you don't
care about, and there's insufficient information to determine whether
this applies in your case). However...

On Mon, Dec 03, 2007 at 02:31:28PM +1100, James Gray wrote:
> Obviously there is the option to tell browsers to use the proxy
> manually, and that will avoid the problem.  However, that is a
> work-around, not a solution in our situation.
>
> So my question to the list is whether or not there is a better way
> to do this (WCCP with Shorewall and Squid maybe)?

Deploy WPAD, via both DHCP and DNS (because Firefox and IE cannot
agree on how to handle it), to automatically deliver the explicit
proxy configuration to the browsers. Firefox users may have to enable
"auto-detect proxy settings for this network" in their preferences,
defaults vary. IE always has it enabled by default. I don't know the
macosx defaults offhand.

Basically it consists of a well-known DNS name and a DHCP option that
both point to a pac file on a local http server. The rest proceeds as
if you'd fed that pac file to the browser directly. It's not strictly
transparent, but it is zero-configuration on the client, which is the
usual objective.

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