Hello. I am currently a child care supervisor and have 24 years experience in the field. I spent 18 years in the classroom and I enjoy working with the children and families. The teachers are likely telling you the truth when they tell you your child is fine and begins playing right after, or shortly after you leave. I see this all the time. It is VERY important for him to know that you trust his teachers and that you are leaving him in a safe place where the teachers will care for him and provide for any needs he may have. Explain to him that it is okay to ask his teachers for help. Good, open communication between you and your child's teachers is key. Have a plan in place with them for drop-off. Have a teacher take your child to the door or window to wave, blow you a kiss. If your child loves the outdoors, leave him in the hands of his capable teachers and have them bring him over to the window to see if they can see birds, trees, is it raining? is the sun shining? I am in ABSOLUTE agreement that a quick drop-off is best. The less time he has to worry about you leaving, the quicker he can get past having you leave him for the day and join in activities with his peers and his teachers. If it would help you, I have the teachers call and leave the parent a voice mail at their office to let them know the child is doing well and what types of activities their child is engaged in. I have found that parents LOVE this! It really helps them feel better knowing that their child has stopped crying, and is enjoying their day, and this is helpful to you, the parent, so you can focus on your busy work day. If a teacher cannot get out of the classroom to call the parent, they call down to me and ask me to call them with a message to let them know how their child is doing. I am a parent and can relate to how it must make you feel to have your child cry when you leave. As parents we all feel a certain amount of guilt because we have to leave our children in the care of others so we can pay the bills among other things. You may not realize it but you could feel somewhat tense whether it be from that or because you begin to feel anxious about whether your child will cry when you try to leave. Children sense these things, particularly with their parents as they are so connected. So my advice is this: Good teacher/parent communication; quick drop off; sense of safety/security for your child. Good luck!