I didn't read all of the responses, but your poor son, and poor you. That's a tough one. I dealt with this with my son, but for swimming lessons. Lucky for me, as of now at least, he is excited to start kindergarten. I think some kids just have a more nervous personality, like my son. Anyway, I felt like when I was in it, I couldn't see the forest for the trees. Obviously it's different, because we're talking swimming lessons for one hour a week, and it's not mandatory--still, I really wanted him to learn because I have a fear of my kids drowning, and our local park has a big pond. So I asked my pediatrician, and he said that if my son is throwing up, he has some serious anxiety and that I shouldn't dismiss it. I don't think you're trying to dismiss it, but I think giving him a cup or bag is addressing more the symptom, rather than the issue itself. Can you go with him to school for awhile in the mornings, until he feels comfortable, then maybe try the bus? You know, baby steps. Did you ever read the book "Real Boys?" Someone lent it to me last year. A lot of the book talks about the pressures society places on boys, and the mixed messages we send them. How they are forced to separate from mom too early at times, and on others terms, and basically told to "be a big boy" about it. The book gave a scenario of a kindergarten room in the first days. If a girl is crying, many people will show her sympathy, tell her it's okay, etc. If a boy is crying, people will encourage him to be a big boy, not cry, etc. But if you stay with him in the classroom a little in the beginning, even if only to usher him in the door, help him talk to the teacher, find his cubby, etc., I think it will go a long way towards helping him to adjust. Because I think just trying to expect him to "get on with it" will only encourage him to stuff his feelings down, and possibly create issues in the longer term. I hope my answer doesn't offend you--I really don't mean to sound judgmental or harsh--you are obviously a good mom for posting this question in the first place. Good luck to you and him.