This: 'cpan install Crypt::OpenSSL' doesn't seem to work

Looks to me that you're using ActivePerl. There are ppm packages (only for 32-bit perls 5.6, 5.8, 5.10, 5.12, 5.14 and 5.16) at the bribes repo.
If you have one of those perls, you can install Crypt::SSLeay by running:

ppm install http://www.bribes.org/perl/ppm/Crypt-SSLeay.ppd
[download]

Tonight I'll build ppm packages for Crypt::SSLeay for the "missing" architectures and put them on the sisyphusion repo.

Update: Crypt::SSLeay ppm packages now added to the sisyphusion repo.

Cheers,
Rob