H.- I am right there with you on this one. My daughter clinged and cried for the first 2 years of preschool, then when she turned 4, it seemed to resolve, for about 6 months, then all of a sudden it was 10 times worse and I couldn't even leave home without her clinging and throwing a tantrum. What I finally found was that a girl in her class that she had been close to moved away and her favorite teacher went to a different classroom. The summer was horrible. This fall I started her in a new school, and she separated fine, a different child, then all of a sudden, last month she started clinging and screaming again. We haven't been able to find the cause, anxiety about kindergarten next year? a boy in her class did leave? One boy does tease her a lot? The teacher told us that she now will cry at the drop of a hat over everything and is very moody, which she is at home too. What works for us is someone different dropping her off. It is a special treat to have Daddy drop her and she doesn't cry for him, he dropped her off for 2 weeks, my mom sometimes takes her, and when i do take her, we talk in the morning about how we want to go in like a big girl and how I will always come back for her. I would keep doing what you are doing and if you can find someone else to drop him off, try it. and look at the environment to see if you can find a cause. It comes and goes. When we go out at night the sitter said she settles down in a few minutes and he probably does too. Maybe set out a reward for him if he can get through a week without any crying.