Windows 2008 Server Not Loading Themes

I have a client whose requirement is that the website we have built for them runs on their Windows 2008 Server box. At the start of the project, none of the technical details had really been discussed, so we did not hit this impasse until last week after the site had been fully sliced out and ready to rock.

The theme loads 100% fine on five different Linux boxes. It even runs okay on a Rackspace carve of the same environment. I had to do some fun tweaks to web.config to get it to rewrite correctly, but now it works 100% fine also.

Now, the client has a guy in-house who is pretty knowledgeable about Windows environment, but no matter what we’ve done, we simply cannot get the theme to load. The closest we have come yet was when I handed over files to him (from my OSX machine) and we had to literally open and re-save every file from ANSI to UTF-8. That sort of did the trick, but tons of stuff was still broken. At the very least, I could see some CSS styling and colors here and there, but overall everything was jacked up.

We’re back to square one at this point, as their tech guy has re-imaged the server. Here’s the site in question: http://ntc.teamnatomy.com/wordpress/wp-admin You will see that the default theme loads up fine. When I activate the custom theme, it throws the less-than-helpful Server 500 error. The theme runs fine on about five separate Linux boxes.

I am at the end of my rope and it is balled up into a knot. Any ideas at all?