Strawberry doesn't help because it still asks for IO::Tty. Cygwin should be a good try according to the Expect documentation.
cpan> install IO::Tty
Running install for module 'IO::Tty'
Running make for T/TO/TODDR/IO-Tty-1.10.tar.gz
Has already been unwrapped into directory C:\PERL\cpan\build\IO-Tty-
+1.10-MfKyq
R
Could not make: Unknown error
Running make test
Can't test without successful make
Running make install
Make had returned bad status, install seems impossible
cpan>
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