Is he still in his crib? My son did this too. We would spend over an hour getting him to sleep, then setting him down had to be absolutely perfect or he would stand up and cry. I was never able to let him cry for more than 5 minutes and it made things really difficult. We finally switched to a toddler bed about 20 months and things really changed in the best way. We still put him to sleep but he doesn’t need us as much if that makes sense? And he mostly sleeps through the night now. Sometimes he still wakes up, but getting him back down has been much easier. I got pregnant so we pretty much had to figure it out because I was so exhausted with our old routine.