Nothing makes me happier than knowing I've wasted hours of their time chasing their own tails.

Is this exposing the underlying OS's behavior coupled with the fact that the IIS document root is `C:\Inetpub` by default? Eight-dot-three filenames are enabled by default on the C drive but disabled by default on all other drives on Windows 10/11:

  PS> (Get-ItemProperty -Path 'HKLM:\SOFTWARE\Microsoft\Windows NT\CurrentVersion').DisplayVersion
  24H2

  PS> fsutil 8dot3name query C:
  The volume state is: 0 (8dot3 name creation is ENABLED)
  The registry state is: 2 (Per volume setting - the default)
  Based on the above settings, 8dot3 name creation is ENABLED on "C:"

  PS> fsutil 8dot3name query U:
  The volume state is: 1 (8dot3 name creation is DISABLED)
  The registry state is: 2 (Per volume setting - the default)
  Based on the above settings, 8dot3 name creation is DISABLED on "U:"