I am having the EXACT EXACT same issue as OP with my 5 month old. I have recently started implementing controlled crying (my version) ie I do not rock or swing or anything him to sleep. He goes into his cot after bath, bottle, book and will usually sleep til 3 or 4 am at which point he has a bottle and goes back to sleep until 6:30 or 7am. His naps however are an entirely different thing. I cannot get him to nap more than 35 mins. It's happened I htink maybe 10 times since he was born. Even as a newborn he hardly slept. I've tried darkening the room (I can't get it completely dark though), I've tried the going in a few minutes before he wakes to resettle him, I've tried putting him down at varying stages of his looking tired phases, all kinds of things. Here is what his typical napping in a day will look like: 6:30 or 7am wakes up and has bottle 8:30 ish I put him down for nap, he cries, I resettle, he cries I resettle and so on...eventually falls asleep 9:00 play or hang out with mummy wherever she is 10 or 10:30 am has bottle 11:00 ish I put him down for nap, he cries, I resettle, he cries I resettle and so on...eventually falls asleep and this is where it all goes wrong: after a half hour he will wake and I cannot get him to sleep any longer. The rest of the day is just him wanting to sleep/play/feed whatever all at the same time because he is actually very tired but will not sleep. Sling doesn't work with him nor does a walk in a pram (anymore). To be honest I want to stay away from the wrong sleep associations and get to a point where he sleeps in his cot when he needs to for the length of time he really needs. After this he may/may not have a nap at 2pm ish and if he does, again he may/may not have a 4th nap around 4-5pm. This all decides when bath, bedtime will be because if he's been up for 4 hours straight I have to get him into bed earlier and if he has too late a nap I have to put him to bed later...this can range anywhere from 6:30pm to 8pm which really is not working for anybody. I don't know what to do anymore...aside from him not getting proper sleep, I basically get zero time in a day to do anything else. At 5 months I'm desperate to achieve something in a day besides a few nappy changes and a bath, if you know what I mean! Suggestions and comments most welcome!