=> Booting WEBrick
=> Rails 2.3.2 application starting on http://0.0.0.0:3000
/var/lib/gems/1.8/gems/rails-2.3.2/lib/initializer.rb:269:in `require_frameworks': no such file to load -- net/https (RuntimeError)
from /var/lib/gems/1.8/gems/rails-2.3.2/lib/initializer.rb:134:in `process'
from /var/lib/gems/1.8/gems/rails-2.3.2/lib/initializer.rb:113:in `send'
from /var/lib/gems/1.8/gems/rails-2.3.2/lib/initializer.rb:113:in `run'
from /storage/git/local_repos/rails/blah/config/environment.rb:9
from /usr/lib/ruby/1.8/rubygems/custom_require.rb:31:in `gem_original_require'
from /usr/lib/ruby/1.8/rubygems/custom_require.rb:31:in `require'
from /var/lib/gems/1.8/gems/activesupport-2.3.2/lib/active_support/dependencies.rb:156:in `require'
from /var/lib/gems/1.8/gems/activesupport-2.3.2/lib/active_support/dependencies.rb:521:in `new_constants_in'
from /var/lib/gems/1.8/gems/activesupport-2.3.2/lib/active_support/dependencies.rb:156:in `require'
from /var/lib/gems/1.8/gems/rails-2.3.2/lib/commands/server.rb:84
from /usr/lib/ruby/1.8/rubygems/custom_require.rb:31:in `gem_original_require'
from /usr/lib/ruby/1.8/rubygems/custom_require.rb:31:in `require'
from script/server:3
Esto se solucionó por completo al instalar libopenssl-ruby
sudo aptitude install libopenssl-ruby