I've never had any luck getting Kynan out of the HAB without waking him up. No matter how long he's been asleep he seems to wake as soon as he feels his head coming out of the HAB... maybe it's the cool air on his face. Sometimes I just go for a really long walk or sit somewhere and let him have his sleep LOL. And it's absolutely impossible getting him out of the HAB and into the car seat without waking!