Perl module Win32::LongPath

use warnings;
use strict;

use Win32::LongPath;

system ('rmdir /s /q test');

mkdirL('test');

for my $i (200 .. 255) {

  my $dir_name = 'test/' . sprintf("%04d", $i) . ('a' x ($i-4));
  mkdirL($dir_name);

  openL(\my $fh, '>', "$dir_name/" . ('_' x 200) . '.txt') or die "$^E";
  print $fh 'Hello!' or die;
# closeL $fh;
}