Ruby require 'file' and relative location
You don't. requires are relative to the current directory, which in your case was GUI_Tests/Tests. If you did this instead:
cd ..spec -r upload_tool -fs Test/test_spec.rbYou would have to use this:
require 'windows_gui' # without '../'The most common way to get around that problem is using File.dirname(__FILE__):
require File.join(File.dirname(__FILE__), '..', 'windows_gui')NOTE: in Ruby 1.9.2 require changed it's defaults: Ruby: require vs require_relative - best practice to workaround running in both Ruby <1.9.2 and >=1.9.2