Right there with you with my own almost 2 DD. We have been working on this on and off for about 6 months with some success. My DD has her toddler bed in our room. I had really hoped to make more progress so far, but she has her own ideas about this. I probably wouldn't care so much except she is such a restless sleeper and I just can't take getting kicked in the face, the ribs, etc any longer. Why does she have to sleep sideways? And what's with her feet having to touch me at all times?? Sorry for the vent, back to the original topic. Our primary goal at this point is for her to go to sleep in her bed and stay there for about half of the night. For a while things went pretty well. She was interested in her bed-we made a big deal about it being her bed (she's been very into "mine"), we made it cozy with blankets, a pillow, some stuffed animals, etc. We followed our regualr bedtime routine, jammies, teeth, 2 stories, singing (usually only when I put her to bed, DH has his own version). We stay with her while she falls asleep, getting her to go to sleep on her own is a whole other phase. And she did well, really well. Would take 20-30 minutes for her to fall asleep and she would stay asleep for 3-6 hours and then crawl into bed with me. If it was on the earlier side I would try to soothe her back to sleep in her bed, but this never worked well, even if she did fall back asleep she'd wake again 15-30 minutes later over and over again. After a while she slept less and less time in her bed. She'd resist going to sleep for longer and longer. We reached 1.5-2 hour marathons of trying to get her to sleep, which included jumping up and down, hitting, biting, kicking, screaming, crying, hysterics and eventually throwing up b/c she was so upset. At first we thought if we just stayed consistent-we'd work through this, but the hysterics and the throwing up upset me and I really don't like being bitten. We caved and brought her back to the "big" bed. After she successfully had her first overnight at my mom's for our anniversay this last weekend (Yay!!!!) we decided the first night she was back to try again. At first she was upset, but although there was some crying there were no hysterics, aggression, etc. I stayed with her and soothed her through it. She slept half the night and then came and got into bed with me. The last few nights there has been no crying, just getting out a little restless energy and settling in, but all in a happy winding down way and she has been able to fall asleep with one of us there in about 45 minutes. We have also been able to just sit beside her for some of that instead of engaging with her (which is good as I am looking to eventually have her comfortable with going to sleep on her own). Last night she did wake up sooner, but I was able to soothe her back to sleep in her own bed in about 5 minutes and she slept for another hour or two before coming into bed with me. So I guess my extremely long winded point is that its a process that has its ups and downs. Don't get discouraged if there are setbacks and follow your child's lead, but don't give up. I find the routine is important, as is lots of attention just before bed. I also suggest if possible putting him in your room, as this just seems like a more reassuring step for your DS. I encourage my DD independence in may ways and many people will tell you that I expect a lot from her for being so young (all of which she is capable of and wants to do) however to have a child this young sleeping down the hall away from me feels "wrong" for lack of a better word. Not that any parent who chooses to put their child in another room is Wrong, just that for me and my DD it is wrong. Hope this helps or encourages you to try and to know that it isn't an all or nothing sort of idea.