I’ve been getting ready to roll out Windows Server 2012 to be used for new production hosts, and one of the first machines I tried to deploy was a web server. I created my VM, installed Windows 2012, got IIS all set up. This web site was to be used for uploading and serving files, so I added a data disk and put the web site on this drive. The web app runs on Perl so I installed that, configured it, and no matter what I kept getting 500.19 errors. I don’t set up Perl all that often on IIS, and I thought for sure that it must have been some quirk in the process that I was missing.
Instead it turned out to be an unholy combination of factors with the way that VMware presents disk drives to Windows and how Windows 8 / Server 2012 handles removable drives. It effects things other than IIS too. The symptoms are strange, the errors are unhelpful, and the fixes aren’t obvious.