You know I do not support the Cry-it-out (CIO) method, and this time I thought instead of criticizing I’d share what works for us. It worked with my first, and it works with my second. It is worth trying and seeing if my Massage-it-out (MIO) method might work for you too. Because it beats CIO in my house.
When my baby seems unable to fall asleep, or unwilling to even try, like it sometimes happens and everything else failed (nursing, singing, rocking, etc.), I start massaging him. I don’t mean a full-blown session that you are probably not even qualified for, just like I am not. I just tell him to lie down for a massage. My son already learned what it is by now and he doesn’t mind trying through his tears and sobs. First I apply more pressure while stroking him all over, because when he is upset I noticed that firmer touches seem to help him relax faster. I do that for a while until I notice he is relaxed and stopped sobbing. Then I start touching him softer and slower, and then even gentler and slower. But it works like a charm now that my son is used to it and knows what to expect. I do it until he is fully asleep, or until he is relaxed enough to let me just sit next to him while he is falling asleep on his own.
This is my personal approach and it worked and works with my children.