My son is 8 now, but I spent many hours worrying when he was 3 – 7. If I could advise my younger self, I‘d say do not put him in Kindergarten until he is 6. We tried it at 5 after strong encouragement from the school and it was a disaster. I put him back in preschool and it was the best thing I could do at that point. He would cry at night and beg me to go to school with him to help him know how to behave. It’s one thing if your child is having a blast misbehaving, but he was having nightmares, etc. It wasn’t all easy after that, he had a tough year and really acted out. In retrospect I think he was terrified of going back to school. The preschool director, a retired special ed teacher, told me she thought he’d end up in an ED classroom! He had a really good 5K teacher the second time, I had to change his 1st grade teacher, but both 1st & 2nd grade were overa wonderful, and he’s a joy. Give him the gift of time to mature and a great preschool that gets boys. I have not medicated my son yet, but I know it’s coming. It will be okay, just don’t get all worked up and worried because it might be a waste of time like all of mine was! God bless!