Test code (run from the Documents directory of a standard OS X user account). d = Dir.new('Pictures') pn = Pathname.new(d) dir = pn.children.find { |child| child.directory? && child.basename.to_s == 'GoPro' } puts dir.inspect JRuby 1.7.5 result: ‼ ⚡ ruby dir_test.rb TypeError: can't convert Dir into String initialize at org/jruby/ext/pathname/RubyPathname.java:201 (root) at dir_test.rb:7 MRI 1.9.3-p392 result: ✔ ⚡ ruby dir_test.rb #<Pathname:Pictures/GoPro> Work-around: pn = Pathname.new(d.path)