I agree he's "testing the waters." What happens, often, is that the victim "allows" the harmless messages, and then the defendant later tries to use it to show that he thought it was OK because you didn't complain before when he contacted you.
Of course, that's not a defense, but it often makes the victim reluctant to report further communication/harassment.
If you want the order, enforce it. It's only a piece of paper, otherwise.