OpenSSL is an interesting case, because it's part of the standard Ruby library, and it should be available in every single copy of Ruby. But Debian faces export restrictions on OpenSSL, so their copy of Ruby is missing a number of important standard libraries by default.

Rubygems can't really clean this problem up, because Rubygems assumes it's running on an actual copy of Ruby, and not a half-broken Debian Ruby.

To get a working Rubygems installation on Debian, I usually 'apt-get install ruby-full', which installs a non-broken Ruby interpreter, and then install Rubygems itself from a tarball so that apt-get stays _far_ away from my Ruby setup.

I don't blame Zed for being angry about this. Debian's Ruby has often been pretty broken even by vendor standards.