gistfile1.txt

# jruby 1.6/1.7:

Timeout 2 triggered

# ruby 1.9.3-p194

Timeout 1 triggered

timeout.rb

require 'timeout'

begin
  Timeout.timeout(1) do
    begin
      Timeout.timeout(2) do
        sleep(5)
      end
    rescue Timeout::Error
      puts 'Timeout 2 triggered'
    end
  end
rescue Timeout::Error
  puts 'Timeout 1 triggered'
end

rubinius 2.0.0dev (1.9.3 d4b69010 yyyy-mm-dd JI) [x86_64-unknown-linux-gnu]

Timeout 2 triggered

Very interesting. I'm really curious of the reasons each one of those possible outcomes would be the "one and only logical one".