We really have to encourage him to do it. I think perhaps it's sunk in now after last year. It's hard for him to do and also he has trouble communicating and it gets worse if he's anxious and/or stressed.
From the standpoint of someone who taught in college (one class - discovered teaching wasn't for me), it is much easier to give a student the "benefit of a doubt" if that student has been asking for help. When you know the student cares, it's just easier to be lenient, if leniency is an option (ie, the subjective portions of the grade).