My son will be 4 in October, and started Montessori three weeks ago. His personality is very similar to that described by the OP. He loves the school and I do too, but today when I picked him up, the assistant from his class told me he was going to be the last of his class to come out b/c he was not listening to the teacher's words today. I wasn't entirely sure what that meant, but when he did come out - walking hand in hand with his teacher, they told me that he would not line up with the others in his class to leave the play area and go into the classroom. Then he would not come to the big rug for circle time. So he had to sit alone and watch the others for a bit and was the last to leave the building. DS told me that he has trouble being quiet during silent time b/c he "just always like to talk." I'm clearly worried. He can be challenging, but until today had done quite well at school. I think I'm going to email his teacher for more info and ask for any advice on things we can be doing differently at home to help him adjust to the M environment. Did any of you who say your child is doing well in the environment have adjustment issues?