> From: [...] Marcus Pedersén
> For my app. I am depending on a windows webserver

For what services are you 'depending' on the Windows web server?  How easy would they be to re-code?
 
Failing that, ISAPI filters aren't too bad - see the JK protocol, for example, which has an IIS ISAPI DLL implementation.  IIS doesn't host Java apps natively either; so I suspect you can use the same range of tricks to serve using Squeak as to serve using Java.

		- Peter