In the daytime my baby mostly contact naps but he sleeps in his next to me crib at night. I’m trying to get him to do one nap a day in the crib but I think we’re in the 4 month sleep regression (he’s 16 weeks) and he can’t connect his sleep cycles. I feed him to sleep and then hold him for 20 mins then transfer him - this is what we do at night and it works well. But in the day he’ll do the 20 minutes in my arms and then after 20 minutes in the crib (so 40 total) he wakes up like clockwork. I’ve tried patting him back to sleep but it doesn’t take, any other tips or will he just get there over time?
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Every baby is different, and he will get there with time, but it’s a question of how much time. Theoretically babies wake from a cycle and want what they had to fall asleep to get back to sleep. If he’s nursing to sleep he may want/need to nurse to connect those cycles in the day because the sleep pressure isn’t as strong as at night, nor does he have nighttime melatonin.

Is baby happy when he wakes up?

when we did it this afternoon he was smiling and chill when he woke up, but when we started playing he was a bit grumpy and yawning again quite soon. He was only awake for 45 mins or so before he was giving sleepy cues and then he napped on me for two hours

exactly what Miranda said - if you’ve associated nursing with falling asleep baby is going to have a hard time linking cycles without that
You can try creating other triggers as well, such as white noise, a short lullaby, or other things. You can start incorporating those and baby can perhaps start to disassociate nursing with sleeping - the best routine to try to get baby on would be a sleep feed play sleep routine rather than sleep play feed sleep
It also might be worth reaching out to a sleep consultant in your area

Baby is still very young. You can try putting baby down right away instead of holding them. Swaddle, white noise and pitch black room might help. I did contact naps for 5 months, so I get how hard it is.