You can break it by having 2 dll's with near identical long filenames that "collapse" to the same 8.3 filename (barring the number at the end: ~1, ~2 etc) and depending on the order you move the dll's into the scanned folder, the 8.3 filenames swap round. Yes, I've had this happen, but it's easy to fix with some judicious file moving and renaming (I may have gone via a drive with 8.3 naming disabled on to ensure the file was "clean" - I forget).