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org.jruby.rack.RackInitializationException: no such file to load -- ...
Do not assume a lib (or any other folder) being on the $LOAD_PATH - make sure its properly added or use absolute requires.
$LOAD_PATH
# config.ru require './lib/myapp.rb' # lib/myapp.rb require 'myapp/helpers' # won't work require_relative 'myapp/helpers' # or # $LOAD_PATH << File.expand_path('lib')