As I understand it, plugins are not reloaded in Rails with each request in development mode. Which makes sense, as generally you add plugins to your app and it\'s the app yo
I have been struggling with this for some time, too. None of the solutions work, including the autoload_paths and autoload_once_paths tricks. Furthermore, the hack with FileUpdateChecker and initializers also does not help (the checker triggers properly, but the files are not reloaded). Same for config.reload_plugins = true...
However, there is a solution. In app/controllers/application_controller.rb add one line:
require_dependency 'your_file_name_here'
The application controller is reloaded on every request and require_dependency makes your file to be checked for modifications and reloaded accordingly. It worked for me, Apache 2, Passenger 3 and Rails 3.0.3.