Looking at the source code, it appears that the Windows Platform SDK defines PATH_MAX as 260, and that is more than 260 bytes long is going to cause problems.

The chdir() in the Microsoft C run-time always does a GetCurrentDirectory() after a SetCurrentDirectory() and it will fail if the absolute path name is more than 260 bytes, even if no single directory name is that large.

There might also be a bug in Perl or the C run-time so that a path name that large overwrites a buffer causing the file names to appear very weird (this is just speculation).

You might be able to get File::Find to work using the "no_chdir" option-- see the File::Find documentation.