Many parents notice a change in their child's sleeping habits when they change them from a crib to a toddler bed because the child learns that they have growing independence and freedom. They can get out more easily. They can go find mom and dad more easily whenever they want. So this makes it difficult to teach a young child how to stay in their room at night. Really, the key, the bottom line is just behavioral modification, persistence. Kids are trained very well and very easily in most cases. They just need to form habits and so anything that you persistently and consistently do for days on end will help your son understand that that's the new norm. When it comes time for bed, develop some sort of routine if you don't already have one, one that will clue him into the fact that it's bedtime. For some kids, this is a bath and then a story. For others, it's rocking in mom's arms with a song. Whatever it is, develop some sort of bedtime routine and stick to it. Do it at about the same time every night and just be consistent about it. You mentioned that he's a big momma's boy so it's okay if you do this routine with him but when it comes time to put him in bed and he's still going to want you to stick around--- and by the way, it's okay if you leave a little night light on if that makes him feel a little more comfortable. Just gently touch his tummy, explain to him in terms he can understand that it's time for bed and he needs to go to bed. Just turn around and walk out of the room. Shut the door; it's okay to shut the door and leave him in there. Give him a few minutes and if he's still crying about 10 minutes later, go in and check on him again or if you have any suspicions that you need to check on him sooner, of course, please do. But if you feel like he's okay, give him 10 minutes or so, go in and gently touch his tummy again. Say "it's okay, mommy's here but you need to go to sleep." Turn around, walk right back out of the room. Do this as often as you feel like you need to but slowly space out the amount of time that you're waiting until you go back in. So the first time, you give it 5-10 minutes. The second time, you give it 10-20, then 20-30, then 30-40, until he's fallen asleep. Again, if you're consistent and persistent about this for 4-7 nights, he should learn that he needs to go to sleep without mom. We're actually going through this with our son, too. He recently switched to a toddler bed and and he loves my husband to lay by him and keep his hand on his back. My husband will lay in there for a half hour with him but if I just go in and put him down, turn around and walk right back out of the room, he knows that it's bedtime because I haven't allowed him to let me do that. So it's all about behavior modification. I hope that these tips help you and if you have any other questions in the future, feel free to ask them on our Facebook page at facebook.com/intermountainmoms and recommend us to your friends and family, too.