Apache and IIS side by side (both listening to por

Question

What are some good ways to do this? Is it even possible to do cleanly?

Ideally I'd like to use packet headers to decide which server should handle requests. However, if there is an easier/better way let me know.

Answer 1

Either two different IP addresses (like recommended) or one web server is reverse-proxying the other (which is listening on a port <>80).

For instance: Apache listens on port 80, IIS on port 8080. Every http request goes to Apache first (of course). You can then decide to forward every request to a particular (named virtual) domain or every request that contains a particular directory (e.g. http://www.example.com/winapp/) to the IIS.

Advantage of this concept is that you have only one server listening to the public instead of two, you are more flexible as with two distinct servers.

Drawbacks: some webapps are crappily designed and a real pain in the ass to integrate into a reverse-proxy infrastructure. A working IIS webapp is dependent on a working Apache, so we have some inter-dependencies.

Answer 2

For people with only one IP address and multiple sites on one server, you can configure IIS to listen on a port other than 80, e.g 8080 by setting the TCP port in the properties of each of its sites (including the default one).

In Apache, enable mod_proxy and mod_proxy_http, then add a catch-all VirtualHost (after all others) so that requests Apache isn't explicitly handling get "forwarded" on to IIS.

<VirtualHost *:80>
    ServerName foo.bar
    ServerAlias *
    ProxyPreserveHost On
    ProxyPass / http://127.0.0.1:8080/
</VirtualHost>

Now you can have Apache serve some sites and IIS serve others, with no visible difference to the user.

Edit: your IIS sites must not include their port number in any URLs within their responses, including headers.

Answer 3

It's impossible for both servers to listen on the same port at the same IP address: since a single socket can only be opened by a single process, only the first server configured for a certain IP/port combination will successfully bind, and the second one will fail.

You will thus need a workaround to achieve what you want. Easiest is probably to run Apache on your primary IP/port combination, and have it route requests for IIS (which should be configured for a different IP and/or port) to it using mod_rewrite.

Keep in mind that the alternative IP and port IIS runs on should be reachable to the clients connecting to your server: if you only have a single IP address available, you should take care to pick an IIS port that isn't generally blocked by firewalls (8080 might be a good option, or 443, even though you're running regular HTTP and not SSL)

P.S. Also, please note that you do need to modify the IIS default configuration using httpcfg before it will allow other servers to run on port 80 on any IP address on the same server: see Micky McQuade's answer for the procedure to do that...