Many thanks, JD. After pondering the page for a bit, I gained some enlightenment about PPM repository usage, and was able to install Crypt::SSLeay from the Winnipeg repository.

And after repairing the damage I did in shooting myself in the foot (installing wrong version of Crypt libraries by hand), it looks like it works! Huzzah!

For any who might want to do the same thing, with ActivePerl 5.8 (ppm under 5.6 has a different command for adding a repository, and you would need to use Crazyinsomniac's, instead of Winnipeg):

ppm
rep add Winnie http://theoryx5.uwinnipeg.ca/cgi-bin/ppmserver?urn:/PPM
+Server58
search crypt-ssleay
install 1
[download]

That ought to do it. The number 1 is probably right, it depends on whether the search came back with other hits (like if you reference Crazyisomniac's repository).