We have been deploying applications to our IIS development server by simply copying war files to the Tomcat webapps dir. When we use the tomcat management consoles upload facility to do the same thing Tomcat always hangs when restarting. The war files are build by ANT on a windows development machine. Are we missing something that is required to upload a war via the management console?
I faintly (& could be imagining it) remember a bug in the ISAPI for IIS a while back that corrupted either binary or large files (or both).
Can you try uploading your war file directly to Tomcat; instead of through IIS and the connector?
Also, if you want some small simple war files to test with, I have a bunch on my own site: http://simple.souther.us. SimpleServlet is a real small 'Hello, World' servlet app. They were all built with the 'jar' program that ships with the JDK.
I faintly remember a bug for deploying .war files using the Tomcat management console on Windows, I think it was in Tomcat 5.0. I'm now using Tomcat 5.5.23 on Linux, and because of a quirk on the project, I have to use the Tomcat management console. So far no problems.