Being a daycare teacher for 8 years, I can tell you that what the teachers are telling you about him being fine 5 minutes later is probably true. I've seen it SOOOO many times. If you're still uneasy with their answer, try dropping him off a few minutes earlier, then hiding around the corner where you're SURE he won't see you ;) and listen to see how long it takes him to quiet down. Or, you could call the daycare 5 minutes later and see if you can hear him in the background. As a teacher, I never minded a parent calling a few minutes after they left to make sure their child was okay. If they do mind, then maybe it's not the best place for your child. They sound very professional and knowledgeable, and you sound like you are doing everything right. It generally takes about 3-4 weeks for a child to become used to dropping off. Some children take even longer. My daughter took about 6 months, then was FINE when I dropped her off, but at first would cry so hard she'd vomit. Every day it was that bad, and it WAS all day long. Good thing I worked there, cuz I knew it wasn't the teachers - they were the best. I'm sure your son is getting great care and it sounds like you're doing everything right. Just try to find a little ritual/routine that you do with him every morning (waving from the window/him shutting the door for you/you leaving a "lovey" of something of yours for him to "hold for you" until you come back, etc.) Children feel safe and secure within routines, so try to make each morning exactly the same so he knows what to expect. Keep up the great work!