Hi! You probably need to start sleep training him. It's not an easy thing to do, but it is so great when they can go to sleep by themselves. He wakes up and starts screaming after 5 minutes maybe because he's overtired and then he can't put himself back to sleep. This is the general course that I followed with my little girl: after a short night-night ritual (book, rock a little, maybe a song), put him down to bed. After however many minutes you can stand (5-10 probably), go in and soothe him. It's better not to pick him up (instead, rub his back, sing to him, etc), but if you have to in order to get him to settle down, then do it. Then, when he's settled, put him down again and leave. Keep doing this. You can wait at longer intervals to go in, or whatever; I think the important thing is that you do what you're comfortable with. He's going to have to cry it out pretty good for a number of days (it varies) before he will learn to go to sleep. With my daughter, sometimes I just thought she'd cried enough and I would end up rocking her to sleep if she didn't go down after an hour or so. But sometimes I'd stick it out. It is really hard to hear them cry, but like I said, it is really worth it. My daughter now is 2; she lies down in her crib and says, "Night-night, Mommy, have a good sleep!" :) You can do it!