Today, I ran into trouble on a fairly fresh installed VM, running Ubuntu. I tried to bundle install and got this stacktrace:

Fetching gem metadata from https://rubygems.org/.Unfortunately, a fatal error has occurred. Please see the Bundler 
troubleshooting documentation at http://bit.ly/bundler-issues. Thanks! 
/usr/local/lib/site_ruby/1.8/rubygems/custom_require.rb:36:in `gem_original_require': no such file to load -- net/https (LoadError)
	from /usr/local/lib/site_ruby/1.8/rubygems/custom_require.rb:36:in `require'
	from /usr/lib/ruby/gems/1.8/gems/bundler-1.1.4/lib/bundler/vendor/net/http/persistent.rb:447:in `ssl'
	from /usr/lib/ruby/gems/1.8/gems/bundler-1.1.4/lib/bundler/vendor/net/http/persistent.rb:216:in `connection_for'
	from /usr/lib/ruby/gems/1.8/gems/bundler-1.1.4/lib/bundler/vendor/net/http/persistent.rb:358:in `request'

Do you need DevOps-experts?

Your development team has a full backlog? No time for infrastructure architecture? Our DevOps team is ready to support you!

• We build reliable cloud solutions with Infrastructure as code
• We are experts in security, Linux and databases
• We support your dev team to perform

Read more Show archive.org snapshot

Obviously, bundler couldn't connect to rubygems.org. Check if you have the Ruby bindings for OpenSSL installed. On Ubuntu, it is the libopenssl-ruby package.