I have spent the past couple of days verifying my web application on windows 2008. One issue that has plagued me is gif files were not served. At first I thought this might be an access right issue since my program is installed under program files. But after adding every imaginable access right to this vpc still no gif would be served. Next I thought it might be caching so I disabled that, but still no image would be served. Finally it turns out that when I installed iis I did not install the static content option. which prevents my .js javascript files and images from being served.