So I'm guessing that there is something that I'm overlooking.

It is a basic trap , there is no dir.exe, which autodie is looking for

$ dir NUL

 Directory of \\.

File Not Found

$ perl -Mautodie=system -e " system q[dir NUL] "
"dir NUL" unexpectedly returned exit value 255 at (eval 10) line 13.
 at -e line 1

$ perl -Mautodie=system -e " system q[C:\\WINDOWS\\system32\\cmd.EXE /
+x /c dir NUL] "

 Directory of \\.

File Not Found
"C:\WINDOWS\system32\cmd.EXE /x /c dir NUL" unexpectedly returned exit
+ value 1 at (eval 10) line 13.
 at -e line 1
[download]

Basically you need to read system followed by Config#sh followed by  help dir at your console, followed by autodie and for good measure perlport#system and How Command Line Parameters Are Parsed and Behind the GUI lives the Shell

See also Re: system() implementation on Windows (again), Re^3: system() implementation on Windows (again)

Yeah, system really stinks, and the sad part is, it stinks everywhere