We've been working with him almost constantly on his behavior. That's part of why I posted this question. It seemed like his whole life was becoming about discipline/reinforcement of good behaviors and discussing what we can do to have a better day tomorrow. It is too much for a 3 year old, and I could tell it was wearing on him, as it was wearing on all of us. We do time-outs, quiet time, marble jars, and discuss his behavior with him thoroughly, always requiring a sincere apology and talking about alternatives to avoid repeating the behavior in the future. I'm fully aware that he's a tough kid, but certain situations seem to make it worse. I think possibly that his teacher isn't as firm with him as she needs to be (such as too many second chances...) He knows how to read people and can easily manipulate a situation. It can be maddening at times. Because of that he has always required very clear boundaries and a routine to help guide him. Any sense that the boundaries may be flexible or that the routine can be altered and he will do everything he can to see how far he can push it. We've been working with his teacher to reinforce his positive behavior through consistent messaging, and things have improved in the past couple of weeks overall, but naptime has continued to be a challenge, one that has remained unaffected by any amount of positive reinforcement or punishment on my part. So my remaining options are to try and suggest ways the school may be able to better manage him, or to just bring him home for nap, but I worry that he will view this as a victory and the behaviors will spill out at other times whenever he wants to go home because he isn't feeling engaged. So I'm still on the fence. There's no school this week, so I have some time to consider what to do.