Patch to add retries to Bundler for Gem installations. Drop this bit in your Gemfile to test it out. Tested with Bundler 1.3.x only

bundler-ssl-retries.rb

require 'bundler/installer'

module ::Bundler
  class Installer < Environment
    MAX_RETRIES = 3

    def install_gem_from_spec(spec, standalone = false)
      retries = 1
      begin
        # Download the gem to get the spec, because some specs that are returned
        # by rubygems.org are broken and wrong.
        Bundler::Fetcher.fetch(spec) if spec.source.is_a?(Bundler::Source::Rubygems)

        # Fetch the build settings, if there are any
        settings = Bundler.settings["build.#{spec.name}"]
        Bundler.rubygems.with_build_args [settings] do
          spec.source.install(spec)
          Bundler.ui.debug "from #{spec.loaded_from} "
        end

        # newline comes after installing, some gems say "with native extensions"
        Bundler.ui.info ""
        if Bundler.settings[:bin] && standalone
          generate_standalone_bundler_executable_stubs(spec)
        elsif Bundler.settings[:bin]
          generate_bundler_executable_stubs(spec, :force => true)
        end

        FileUtils.rm_rf(Bundler.tmp)
      rescue Gem::RemoteFetcher::FetchError => e
        if retries <= MAX_RETRIES
          Bundler.ui.warn "#{e.class}: #{e.message}"
          Bundler.ui.warn "Installing #{spec.name} (#{spec.version}) failed."
          Bundler.ui.warn "Retrying (#{retries}/#{MAX_RETRIES})"
          retries += 1
          sleep retries
          retry
        else
          Bundler.ui.warn "Installing #{spec.name} (#{spec.version}) failed after #{retries} retries: #{e.message}."
          Bundler.ui.warn "Giving up"
          msg = "An error, most likely because of network issues, has occurred trying to install #{spec.name} (#{spec.version}), "
          msg << "and Bundler cannot continue."
          raise Bundler::InstallError, msg
        end
      end
    rescue Exception => e
      puts e.backtrace.join("\n")
      # install hook failed
      raise e if e.is_a?(Bundler::InstallHookError) || e.is_a?(Bundler::SecurityError)

      # other failure, likely a native extension build failure
      Bundler.ui.info ""
      Bundler.ui.warn "#{e.class}: #{e.message}"
      msg = "An error occurred while installing #{spec.name} (#{spec.version}),"
      msg << " and Bundler cannot continue.\nMake sure that `gem install"
      msg << " #{spec.name} -v '#{spec.version}'` succeeds before bundling."
      Bundler.ui.debug e.backtrace.join("\n")
      raise Bundler::InstallError, msg
    end
  end
end