Joel's having trouble with IIS. This is -exactly- why good admins hate windows. Most of the debugging he's done has only been so focused because he's an experienced win32 developer. Most admins wouldn't even have gotten this far.
Windows just has a lot of hidden complexity (black magic). Which is fine when it works, but when it breaks, look out. Where is "truss"? Where are the detailed logs? Where is the detailed documentation? It's just too complicate to troubleshoot effectively. I always think admins of any system get better when they know the programming model and detailed information about their platform's implementation, but they shouldn't -have- to know that in order to troubleshoot the simplest of problems.
This is why windows gets a bad name in reliablity; a ton of admins know nothing about how it works behind the wizards and property sheets, so they can't troubleshoot it effectively.
I guess I'm saying that what you gain in productivity from easy out of the box setup, you almost always lose later in frustrating troubleshooting sessions. In unix, this problem would be solved conclusively with a single truss/strace command (or Dtrace if you're lucky enough to be running Solaris 10).
Sadly, I luckily haven't had to deal with IIS > 5 much (or at all), so I can't help Joel out here.
Widows debugging tools are gflags.exe and WinDBG.exe
Oh, and it looks like Joel got it fixed.
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