At home, I have a mixed network with Linux and Windows computers. I have a cable Internet feed and, currently, am using an appliance firewall (Linksys WRT610, running Linux IP Tables "under the hood"). However, I am considering installing a configurable firewall (Endian, Smoothwall, ClearOS, or IPCop) on a Linux box.

Here's my question. I have an Apache web server running on a Debian box, and on a separate box I have Windows Home Server, which also does web serving of a sort--specifically, WHS provides a secure remote access portal allowing me to remote in to my network from anywhere on the public Internet.

My dilemma is that both the Apache web server and the WHS web server have the capacity to serve web content over SSL (so inbound on port 443), and port forwarding on the firewall has no way to know whether an incoming packet arriving on port 443 is bound for the machine running Apache, or the machine running WHS.

What I would LIKE to be able to do is to sort packets inbound on port 443 based on the URL--meaning some type of text or string-based matching on the URL and, depending on the match result, route that packet to either of the two separate IP addresses on my network (for the Linux Apache box or the WHS box).

I'm not sure how to achieve this, though, and would appreciate any hint or guidance that anyone has. From my (limited) understanding of IP Tables (which are behind Endian, IPCop, etc.), I don't believe that IP Tables in a firewall will be able to do this type of sophisticated routing.

What do I need? Some type of filtering or redirection utility? Like Squid or something? Any hints, suggestions, or tips as to where I might get started would be greatly appreciated.

nope, not possible. The HTTP data is inside the SSL, so you'd need to terminate it etc...

put a proxypass directive under apache and proxy the WHS requests through to windows

Thanks for the suggestion, Chris. I'll look into an Apache proxypass directive. I was thinking of attempting some type of redirection at the firewall using Squid or one of its plug-ins, but the Apache proxy idea sounds much simpler.