Is he getting more mobile? Teething? Do you lay him on his tummy?: Just pretend I didn't recommend it ok?: Usually it's either something like teething/growth spurt or it's developmental. When they get more mobile and their little brain goes to the next step something happens where they wake much more easily and much more often. He sounds a little young for this but if you feel he's a little advanced then that's probably it. I know, it's hard and no fun. It kind of just has to pass. Maybe you can try drinking some strong chamomile tea starting in the early afternoon and he'll get it in your breastmilk all night. Also, you can give him a bath with lots of lavender to help relax him at night. Other than that all I can say isI can total relate to the racoon eyes phases. I hope it gets better soon. Try to nap whenever you can. I know, easier said than done. Hang in there.