G.P.
Sorry, I haven't had the chance to read the other responses, but here is my two cents. My son goes to daycare, and I find that he really picks up on my response to the teachers. There are two I REALLY like and one that bugs me. Whenever I leave him with the one that bugs me I hear him crying all the way down the hall. With the others, he may cry for a minute or two, but then is okay. When I made an effort to be really friendly to the one that bugs me, he did better, not great - she may bug him too, but better. When I go to drop him off, I spend a few minutes getting him settled and get some toys and then I say goodbye and leave. If you act like it is a bad thing to be leaving him, or extend out the goodbye, it will be worse for him. Just say goodbye and leave...it is easier. He will get used to it. (it's actually harder on you than him)