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I've set up Rack::Reload according to this thread # config.ru require 'rubygems' require 'sinatra' set :environment, :development require 'app' run Sinatra::Application # app.rb class Sinatra::Reloader < Rack::Reloader def safe_load(file, mtime, stderr = $stderr) if file == Sinatra::Application.app_file ::Sinatra::Application.reset! stderr.puts "#{self.class}: reseting routes" end super end end configure(:development) { use Sinatra::Reloader } get '/' do 'foo' end Running with thin via thin start -R config.ru , but it only reloads newly added routes. When I change already existing route, it still runs the old code. When I add new route, it correctly reloads it, so it is accessible, but it doesn't reload anything else. For example, if I changed routes to get '/' do 'bar' end get '/foo' do 'baz' end Than / would still serve foo , even though it has changed, but /foo would correctly reload and serve baz . Is this normal behavior, or am I missing something? I'd expect whole source file to be reloaded. The only way around I can think of right now is restarting whole webserver when filesystem changes. I'm running on Windows Vista x64, so I can't use shotgun because of fork() .

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