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Have you tried comforting him in the crib until he falls asleep instead of fully picking him up? Shushing, patting his back, etc.

Have you tried putting him down with a paci? Or try holding him for 10mins while asleep so he gets deeper?

Try putting him down and then shush-patting him. My LO always responded to pats on the butt (she was a side sleeper) and prior to the side sleeping, I had to rub her tummy.

I think they do sense when you are putting them down, so don't wait till your LO falls asleep and then try to creep him into bed, just put him down in the crib as soon as he's drowsy and either shush-pat or pat, or sing a lullaby and pat. We used to have to do that a full 5 minutes or so for our LO to sleep (which is an eternity when you are hanging over a crib!), but 5 minutes is better than 2 hours.

We had a very similar experience. For a while we would wait until she was really really asleep- like 15 minutes minimum after she seemed asleep- to put her down. But sometimes even then she would wake up and we would both cry. Like your Lo, patting and shushing while she was in the crib just made her more upset. Is the bed cold when you put him down? Maybe a warm receiving blanket tucked tightly around the mattress would help? The LC in my hospital suggested having it tucked under your shirt while you nurse then ticking it in the crib before you put baby down but I think you would need your so's help to get it safe and tight.

Eventually we had to do some CIO at bedtime. It was really hard (on me) because she was so young, but she was actually crying less overall because she was getting so upset before.

I've been putting my guy down lately in his crib still awake then giving him a bottle (of breastmilk ) until he falls asleep. To avoid the same issue of waking up when I transfer him...