re: What do you do when grounding doesn't work?

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He is a very, very well liked kid. He's also overall very happy, albeit sometimes stressed about grades. With the exception of two friends that were removed from his circle after the car-theft situation (one went to in-patient rehab and the other left to go to another school) His friends would be considered the popular boys, with girlfriends, nice homes, intact families, highly functioning kids. These are not the seemingly 'troubled' kids you would see in an afterschool special. He generally rolls over when he gets punished, but then he fricking does it again.

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Then I think you are over-reacting.

He certainly needs to have some consequences, and you don't want him to do anything dangerous, but this sounds like normal high school shenanigans to me.

Me, and all of my friend group, did all of those things and more and everyone turned out fine.