Fear of Preschool Carpool Dropoff

Could there be a kid there in the drop-off area that said something to him? Have you talked to the PE teacher? Does he not like the gym at all or just in the morning?

give him a reward for being a big boy and car pooling

preschoolers get upset about the unknown and it is probably unsettling for him. He has to deal with lots of other children and teachers in the gym and may fear not knowing what could happen to him. I would ask the school if you could park on the side for a few weeks and walk him into the gym so he gets settled. then talk to him about what bothers him about it.

He's only four -- I know it's inconvenient, but I might just give him some more time to grow into it. He might need you to feel secure right now.

If he's been OK with the process in the past and he hasn't had something happen to change his mind, then it really sounds like a power struggle. Kids can, and do, work on our Mommy feelings to get what they want, sometimes just to see what they can get away with. I would explain that you expect him to be a big boy about it, and just do it. The fact that he's "insisting" you get out and walk him in is a clue. You apparentlydid it already because he insisted, and now he's very impressed with his power and doesn't want to go back to doing it your way. Get in line, get out of the car and get him out of his carseat if necessary, kiss him good-bye, and leave. If you are trying to coax him, or encourage him, or bribe him---stop. Be very calm, but show him this is the way it's going to be. He'll be fine.

It doesn't sound like he's doing this "all of a sudden" - since you walked him in all last year. He liked that, and wants to stick with it. If I were you, I would let the teacher take him, kicking and screaming. Like someone else said, it's harder on the mom (it really is!!) I would just tell him that this is how it is done. Definitely nip this in the bud before he has to get on a school bus :)

To be honest I would let the teacher take him and let him cry. I can't tell you how many moms in my years of child care would stay, and stay, and stay, when their child cried, trying to make the feel better about staying. As soon as they left the child stopped crying and went to play. They usually didn't cry again until mom came to get them, and if it was dad they never cried at all.

It is harder on the mom than the child. He will adjust.

Is he missing that last hug and cuddle? Can you do it before you leave the house? Try talking to him and talk him through the whole process...you will give hugs and cuddles, get into the car, drive to school, another hug and cuddle, teacher will open the door and take you to the gym, and then you will all walk together to the classroom. This way he knows what is coming and you can try to see if he has any fears upfront.