How long should I let my 5month old cry? Lately he has been horrible with napping, no, I don't spoil him, but he just will not take a nap no matter whether I'm holding him or lay him down or anything I try. So I put him in the crib and he's crying and screaming. He's been fighting his sleep lately except at night so I don't get it, I can tell he's tired . 😞