OpenSSL-Pharo now works on Windows. Tested on Windows 10 with a fresh 32-bit Pharo 6.1 zip package downloaded from pharo.org. On Windows this library uses libeay.dll which is bundled with the Pharo VM.

Metacello new
  baseline: 'OpenSSL';
  smalltalkhubUser: 'PierceNg' project: 'OpenSSL-Pharo';
  load.