A., You need to get out of his bed! I did that with my first, and when #2 came along, it was a mess! Try sitting in a chair next to the bed. I took 2 weeks to train my son ( he was the same age as yours ) First i sat next to the bed as he cried, i'd talk to him, but not get in the bed, or pick him up. If he got up out of the bed, I'd leave the room...one night of that, and he stayed in the bed. Night 3 or so, quit talking to him...maybe hummmm. then a few nights later, do bed routine, and be quiet. Few nights later, move the chair towards the middle of the room...few nights later by the door. It was two weeks of agony for me, but I now have a little boy that I can do bed time routine with, give a last hug and kiss, and walk out the door...I also did this method with my 2nd and 3rd, and so glad that I did. The books say to do this method in a week, but my son was like yours...standing at the gate screaming but he didn't vomit, he'd hold his breath till he passed out. It is a struggle for both of you, but the end result is worth it...espically when you are going to be tired and have your new baby needing the attention too. You won't be able to lay down in his bed with a newborn! It is also nice when you go to spend the night at someone elses house too...we've had friends from out of town stay with us, and OMG I couldn't believe how hard of a time they had getting thier little one to sleep. she may as well have gone to bed with him, cause it ruined the whole rest of her evening. Be firm, they need to learn to get to sleeep on thier own. Good luck to you!