I've noticed with my daughter as soon as she starts yawning that's when I start getting her ready for bed turn the lights off the fan on feed change read to her rock her with her pacifier till she passes out and I put her in the crib

My Daughter Has Been Doing the same thing since birth and I always gave in and rocked her to sleep like she wanted and still had to do this at 1 years old I finally got fed up and at night I would give her a bath , her cup of milk and lay her in her bed turn all lights out and walk away , she cried but I had to let her , I would walk by her room every 10 mins , make her lay back down and eventually she fell asleep Dont give in mommy I'm upset it took me a year in a half to finally stop this but its been great ever since

I wanted to add if he cries for more than a half hour then you should pick him up then but only hold him for a few minutes so he can calm down.

Give him a bath and feed him, then put him in his crib. If he cries wait five minutes, then go in and reposition him and put a paci in if he uses one. Pat his butt or rub his back. It is important that you don't pick him up. Continue to do this every five minutes if he continues crying until he is asleep. This is what everyone on my family has done for generations and it has worked well. My son started sleeping through the night at 4 months. Also, he could be teething. Maybe you can give him something to relieve pain. We all know it sucks trying to fall asleep when you are hurting! Goodluck, Mama! We are all here for support.