A minute ago I had problems running the cpan install of Crypt::SSLeay under Windows + StrawberryPerl:
cpan -i Crypt::SSLeay
Before I tried the cpan module install I downloaded and installed openssl and Microsoft Visual C++ 2008 Redistributable Package. When cpan asked me where I installed openssl I pointed it to the right directory, but still - whenever it came to tests, all tests failed!
Here is the solution: To keep my system tidy I chose "copy libraries into OpenSSL's /bin path", which the openssl installer offered. Anyway, with this option the cpan installer/testing script fails! So I bit the bullet and installed OpenSSL again, now with the DLLs in the Windows directory, and tataa! it works.