I couldn't do cry-it-out either, so I'm totally with you there. I also did the 5-10-15 routine, slightly modified. I'd pick up my son (which I know is a big no-no, but there was no other way to stop him from crying!) and either read him one book or sing him one lullaby. That would calm him down again, and I'd put him back down. After the 20 minute rotation, I'd give him another bottle, and that would knock him out. I think it took about 2 weeks of this routine before he'd put himself to sleep with little to no fuss. He's now 21 months, and he does regress sometimes (actually, we just finished a three-week spat of screaming-fits-at-bedtime), but I've found that the single story/lullaby knocks him back into shape. Er, sleep. I do think it's significant that your daytime sitter says she's putting herself to sleep at naptime. Because of this, I'm kind of inclined to say that your daughter is putting you on. She knows that if she screams loud/long enough, you'll bring her to bed with you. She also knows this trick doesn't work on the sitter. Which means: if you want her to stop sleeping in your bed (which you say you don't mind, but then you say you do, and have you seen the number of posts lately about parents wanting their 2-year-olds out of their bed? TAKE NOTE), you need to STOP LETTING HER SLEEP THERE. Period. No backsliding. Yes, it's going to suck. No, you're not going to sleep real well for a few nights. Yes, your daughter is going to think you are the worst parent ever. (My son tells me this often.) Yes, it will work. Yes, I swear, I promise, I really mean it, it's worth it. I think your basic routine sounds fine, if a little long (it shouldn't take more than 20 minutes). I think you need to add in a few modifications until you find what works for you. Maybe cut out the bath every night (unless she's got skin issues, every other is fine). Maybe the massage isn't working for her. Maybe she'd like some white noise in the background - or no noise at all. Maybe she needs more light, or less. Maybe she really does want that bottle after the 15/20 minute cry. Better yet - what does the babysitter do for naps? What do you KNOW works? Modify that for bedtime, and see how it goes. Good luck!