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I think what I am after is a proxy server ...

I have some web applications written in Python for a small scale deployment on a Windows machine. I was envisaging each web app running its paster instance on a different port and a front end proxy server redirecting ordinary requests to say to and to

I need it to be pretty simple configuration, preferably through a GUI or webinterface since it will be left in the hands of not so techie types.

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Nginx, haproxy, and squid are probably the most commonly used for running reverse proxies, but all of them focus on caching and/or include at least a minimal HTTP server. Since it sounds like you need neither of these things, but rather just something to forward requests to the right host/port running IIS, you could look at pound reverse proxy. It should do what you're looking for and although it can be installed on just about anything but Windows, it's not difficult to configure on an old "beige box" at or behind your WAN gateway that should keep the complexity to a minimum. No gui, but there is a live CD of Pound based on FreeBSD out there that's easy to get up and running.

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I haven't tried specifically what you're asking, but I would probably start by looking at Apache and mod_rewrite.

Of course, Apache is not one for 'simple configuration', but there are some GUI managers out there.

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This is not quite what you want, but it does explain why it's not as simple as it looks at first glance:

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