Baby crying to sleep?

Hi all. Just wondering how your baby goes to sleep either naps during day or the bigger night ones? My baby cries himself to sleep even whilst I’m cuddling him and feeding. It’s like he is fighting it and then eventually goes to sleep from exhaustion or giving up. Anyone else have this or advice?
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In the day it's walks out in the pram or a car walk. Won't settle in the cot (but need him to self learn). At night he self settles but we spent some time encouraging/ practicing this as it was the only way to get through the 4 month sleep regression. I've dropped the contact naps as he wouldn't settle anymore and we had so many overtiredness dramas. I'm a bit nervous teaching him to self settle for day naps as he's impossible to calm down but I know eventually I need to do it, especially approaching 6 months x

My daughter will cry at night even when feeding and I just cuddle and shush, she's restless and like she is fighting it. My eldest was the same, but the 2 in-between would just lay down close eyes and sleep lol. I think it just depends on the baby! X

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