There are ways to automate Windows testing with Perl... You bettcha!
Amongst other things, take a look at Win32::GuiTest. I was looking for screen shots on the web and came across this:
Win32::GuiTest
CPAN Win32-GuiTest readme
another automated Win32 GUI testing article
I'm sure that you will get other ideas here also.
Search Google with: Win32 Gui test.
Update: Ooops.. it appears that what is needed for this app is just some control from/of the Win shell. And yes, Perl can do that.
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