Sorts a bunch of lines like this: Redirect 301 /foo/bar http://stuff Redirect 301 /foo/bar/baz/ http://stuff in a way that means that the more-specific paths appear after the shorter ones, with some intelligence.

sort_redirects.rb

#!/usr/bin/env ruby1.9
# Sorts a bunch of lines like this:
#    Redirect 301 /foo/bar http://stuff
#    Redirect 301 /foo/bar/baz/ http://stuff
# in a way that means that the more-specific paths appear before the
# shorter ones, with some intelligence.

require 'set'

class Redirect
  include Comparable

  attr_reader :cmd,:status,:url,:dest,:line

  def initialize(line)
  	@line = line
  	(@cmd,@status,@url,@dest) = line.split
  end

  def <=>(other)
  	my_set = Set.new(@url.split("/"))
  	their_set = Set.new(other.url.split("/"))
  	if my_set.subset? their_set
  	  return -1
	elsif their_set.subset? my_set
	  return 1
	else
	  return @url<=>other.url
	end
  end
end


ARGF.readlines.map{|a|Redirect.new(a)}.sort.reverse.each do |a|
  puts a.line
end