This isn't related to Perl. Windows had problem with running non-executables with redirection. I thought that was a thing of the past, but I guess not. I've had no problem with WinXP and Win7 with a wide variety of ActiveState builds, but my system isn't setup in a way that allows omitting the extension. Maybe the problem lies with that feature. You might have better luck specifying the extension. If that doesn't help, you'll have to specify the executable. You also have the option of using pl2bat.