What did you expect to happen? ruby.exe is the ruby interpreter, meant for running ruby scripts. Normally, to use it you would create a file containing valid ruby commands with your favorite text editor (but not a word processor). If you save the file as foobar.rb, typing ruby foobar.rb (or if you told the installer to associate .rb files with ruby, typing just foobar.rb) will execute the commands in the file as a script/program. If you don't supply a script file name, ruby goes into input mode and expects you to type in a program on the spot. It won't give any feedback until you indicate end-of-file by typing CTRL-z, at which point it will process what you typed and most likely tell you about all the errors you made. If you want line-by-line interactive feedback, use irb.