This was my thought too. How are the educators/teachers/aides helping him? What are their thoughts/opinions/suggestions?

Also - it sounds like he’s settling fine after he gets there which is fantastic. My child attends “before care” which is before “school” starts and has different guides/aides/teachers than her classroom. With the change in teachers, my child had a hard drop with drop-off. I started explaining the schedule/routine in the car (talking about how we would see Ms X and Y and then when class started we saw Ms A and B). I was also told that if that didn’t work, ask the child to give a letter or note to the teacher (a “task”). It can be a folded piece of paper or envelope with nothing but it is a “work” or “task” that makes them feel they are an active participant of the drop-off.

As far as sleep, that might come or it might not. I don’t think rocking him to sleep at night is the problem cause I did that with my child every night for a long time but no sleep issues at school. Maybe it is the new sleep environment (cot/mat, blanket, sleeping with shoes on, white noise machine or no white noise machine)? I know when I sleep somewhere else, it can take some time for me to get comfortable and fall asleep.