The Middle-of-the-Night Cry Every Mama Needs to Know. You’ve finally put your head down on your pillow and no sooner than you start to drift off to sleep, your baby starts to cry. Sigh…. Whether your baby has been in bed for one hour or four hours, your first thought is “Why is my baby crying?”. Whether it happens before or after midnight, or many times throughout the night, you do the same thing.