(You overwrote your original inquiry with a new inquiry. You shouldn't do that. Now, our responses to your original question don't make any sense in the new, changed context.)

No, I don't know why OLE automation using Perl and Win32::OLE doesn't work under Cygwin. But more importantly, I don't understand what you gain by using Cygwin, "a Unix-like environment and command-line interface for Microsoft Windows" (Wikipedia), in tandem with a Perl script to manipulate Windows-only software. What Unix software do you need to use with OLE automation? To me, the two technologies are discordant, but I admit I don't fully understand either Cygwin or what it is you're trying to accomplish with it.

Jim