You set up @recording in your before block, but the code you have posted for your run method will not use that @recording instance and therefore the call to recording.import in the run method will not raise an exception.
In your run method, recording can either end up being an instance of NullAsteriskRecording or AsteriskRecording. If you know that it is going to be an AsteriskRecording as your current test implies, one approach would be to change your before block to the following:
before do
AsteriskRecording.any_instance.stub(:import).and_raise("error")
end