my son also did that. thank god it wasn't that high of a bill. What I did was after the extreme grounding at home, I went down to the local police dept and explained the situation and they were more than happy to help "explain" it to him. They came over and really scared the crap out of him. He got a tour of the juvy center (which really bugged his sensory issues) and then he did some "light" community service picking up trash. Not gonna say he's perfect or hasn't got into trouble since but he didnt do that again.

I'm sorry you're going through this. I know how horrible it feels. The EXACT same thing happened to us several years ago with our older child on the AS--he was about 11 or 12 at the time. His whole world is/was computers and games and he used my Paypal account (remembering my password from watching me type it in) to buy online access to a game. This happened right before Christmas (and his birthday which is Dec 22) when I had already purchased video games and a new laptop for him. We were devastated by what he had done and also struggled with what to do. We really wanted to make an impact on him so he understood the severity of his actions and also wanted the punishment to fit the crime.
Here is what we did, and yes, many people can say how harsh it was and overboard, but it made more of an impact overall--even on his general behavior--that I'm so glad we did it:
I got out his Christmas/birthday gifts which, again, were video games and a laptop (he begged for a laptop for several years and had no idea he would finally be getting one). I showed him the laptop so he saw that it was almost his and he sat there while I called Dell and arranged for a return. Then, he went with me to the different stores so we could return the video games. He lost his computer privileges for several months unless it was for school work.
We did still get him Christmas and birthday gifts--I'm not heartless lol---but the video games he got were learning games like Brain Age and memory games. If he went on a website that wasn't school related, it was a learning website for math games or learning to type games. He also had to pay us back with allowance and money he got for Christmas and birthday.
It tore my heart out to be so "cruel", but that punishment was a turning point for my son. He still refers to that time and the impact it had on him. His whole general attitude changed for the better in an almost miraculous way.
Anyway, that is what we did. Hopefully, my story can help you if even just a tiny bit. Please keep us posted!

Faith- I was just telling my 10 year old tonight that if he stole anything ever again I would call the police myself. I'm glad to know that they would help me out with that.

Be proud of his smarts... and be proactive in teaching him about law. Rules are there so we can help each other. Help him brainstorm ways to access things he wants, within the rules.

I can totally relate to your situation.

Add very public embarrassment. In 10th grade he hacked the high school firewall and was watching pornography during study hall. My husband and I are both teachers... our jobs were precariously perched after that little incident!

He lost computer privileges at school that year, except for brief and closely supervised research for papers. It was gradually returned as his grades and demonstration of responsibility in other areas merited it.

He totally lost computer access at home, and we restricted the tv to G rated only through password locks.

He had to gradually earn back each little step of ratings on tv, time on computer, etc. through LONG checklists of tasks, responsibilities, etc.

Last year, he took my debit card from my wallet... and learned the hard way about bank theft protections. We didn't have him arrested, but he found out that plastic becomes useless very quickly when someone knows it has disappeared. My card magically reappeared in my wallet two months after disappearing. I had known it was him because the couple of charges prior to lockout were at the school snack bar.

We kept password locks on R,NA/AC and MC ratings on the tv, and changed them every couple of weeks, all the way through him leaving for college.

He knows the consequences, and is very determined NOT to lose his college experience.

Because we were firm, consistent, and provided natural, logical, intense consequences, he is moving into adulthood with a clear picture of cause-effect (positive and negative) for his own choices.

He earns allowance, $5 a week for doing basic things like emptying the dishwasher, moving laundry, etc. And we rarely tell him no on games and things but he does have to earn them. If he has the allowance for it, I do ask him to really think about his purchases but really don't tell him no unless he doesn't have money for it and then he just has to save up. He's saved up to get the full pc version of Plants vs. Zombies ($20) and other things that are pricier so I don't understand why he felt he had to be sneaky about this.

I'm really trying to be calm about it but railed into him yesterday when he came to me saying "I wish I wasn't on restriction." OMG! HE JUST stole all our grocery money and I just lost it. His dad came home and talked to him about how we all make mistakes and that it doesn't make him a bad person but that this is serious and there has to be consequences for it. I've given him lots of hugs and tell him I love him so he knows that too. He's not a bad person, he just did a bad thing. We just have to make sure that it doesn't happen again.