Replicated with Perl being discovered as follows:
['C:\\perl\\bin\\perl.exe', 'c:\\cygwin\\bin\\perl.exe', 'c:\\perl\\bin\\perl.exe']

C:\perl\bin\perl.exe is installed from ActivePerl-5.16.3.1603-MSWin32-x86-296746.msi

Attempting to compile Python 2.7.6. Installed Python binary used to run build_openssl.py is Python 2.7.1.

As mentioned the call to the file handle's close returns 1 for every perl installation.

In this version of ActiveState Perl the errorlevel from running Perl with a successful command is 0, and with an unsuccessful command is 2.
perl -e "use Win32;"
echo %ERRORLEVEL%
 ==> 0

perl -e "use Win32x;"
echo %ERRORLEVEL%
 ==> 2