So my son has this thing where he falls asleep on our bed and then I move him to his crib. He then…

So my son has this thing where he falls asleep on our bed and then I move him to his crib. He then proceeds to wake up so I bring him back to give him his bottle so he falls asleep again and then I move him once again. Although, the min I place him back in the crib he wakes up crying for me. I'm currently allowing him to cry it out bc he's making it a bad habit and i will not tolerate it. Anyone else going through this atm? How long did it take for your LO to break the bad habit?? (My son will be 10mths this weekend).