Update: There is now an update available via KB2811670 from Microsoft to address this (thanks Owen).

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.

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