Over time i have collected several ruby related textmate bundles which i have enjoyed tweaking for easier usage. During this time I somehow managed to mangle my file type recognition settings. I first noticed this problem by losing the ability to use the shortcut keystroke to execute rspec tests.
The solution lies in this textmate blog post: http://blog.macromates.com/2007/file-type-detection-rspec-rails
In summary i did the following:
Closed textmate completely and deleted the related manual textmate bindings for these languages with the following command in the terminal:
defaults delete com.macromates.textmate OakLanguageFileBindings
Next I changed the way textmate viewed ownership of the .rb file extension. I specifically revoked it from the Ruby bundle and enforced the ownsership in the RubyOnRails bundle.
Opened textmate and navigate to Bundles -> Bundle Editor -> Edit Languages and added rb to the Ruby on Rails grammar's fileTypes array so that it reads:
fileTypes = ( 'rb', 'rxml', 'builder' );
Note: These are the values in my RubyOnRails language settings. Yours may differ but the important entry is 'rb'. Make sure its included in the list.
Next, I navigated to the Ruby Bundle -> Language settings in similar fashion and REMOVE the 'rb' file type from the list. There was a large amount of text to sort through in looking for this setting so i simply copied all to a text window, searched and replaced then pasted back into the textmate language definition window.
At this point the filetypes were registering fine for rspec tests and ruby/rails filetypes. I checked this by watching the status bar - filetype setting display.