You are describing my DS.
I have an older DD so I know I'm not doing anything wrong.
He walks to school so happily, then sort has a freeze at the gate. Lip wobbles, keeps turning round to me, starts mummmeeee
In our case, what makes it worse is new terms, changes, long weekends or sick days. If we had an extra fun weekend or he was all cuddled up and happy before being told to get ready for school.
It's like he forgets he has to go to school. And he doesn't know what day it is yet.
He never kicks off on childminder days (2 per week).
He is better when I am on time and he lines up than going in alone (still on time but teacher gone through).
He is better with a long build up of it's school tomo, I put your uniform out so be good and see how fast you can get dressed for me in the morning.
I bribed a week of sticker chart on front door for no tears week one and smiles week two. He chose a toy, we bought it together.
He is struggling a little in school. Huge writing delay, slightly behind in phonics but reading within normal range.
Friendships are tricky. His speech is actually very advanced for his emotional maturity (poss linked to writing delay issues) and he often says he has no one to play with. I think he's bossy and his rules too complicated.
But he is a friendly chap and he does have a best friend. Everyone says hi to him.
His teacher is young, weak but keen so not much help with anything useful.
I don't have the answers. But I'm happy to have a friend to share my woes with!
DS is a Gemini. He certainly has two sides to him!