cry it out

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Has anyone successfully gotten their baby to fall asleep on their own? I want mine to be able to so that when he does stop nursing he knows how to get to sleep. The leave and check method just gets him more and more upset so does me picking him up and putting back down afted he calms. Cry it out would be best for my baby and has worked in the past but now he refuses to go to sleep! How long is too long to let him cry it out? Who has been successful with this?