If you are building Ruby by hand on Debian and you need OpenSSL support, make sure to install the libssl-dev package (sudo aptitude install libssl-dev). The tricky part is that even if you don’t install it, configuring the Ruby build with OpenSSL (./configure --with-openssl ...) will not complain that the necessary libraries are missing. Why? Here is someone’s guess in the ruby IRC room (I can’t remember if I was in ruby or ruby-lang):
peshalto: I remember long ago when encryption libraries were always supplied as stubs to deal with export restrictions. not sure if that's still done today. with a fake library stub in place, a compile would go along happily and you'd never know that the encryption was disabled. peshalto: could that still be the case today? i wonder if it's picking up a stub from somewhere and not finding the real library you installed.
