Likes crate but doesn’t go in voluntarily

My ~5.5 month old puppy has never had an issue being crated at night and has been sleeping through the night since he was about 16 weeks. We worked hard to make sure he views it as a safe space and he will dip in and out during the day to get toys, etc. but never settles himself for naps or takes himself to bed there. He’s even developed a frustrating (but cute, tbh) habit of going to lay down on his living room bed when he knows we are trying to put him in the for the night and looks at us like “bedtime? who, me? Look how sweet I’ll be laying right here 😇”

Am I over-indexing on wanting him to go in of his own accord even though he will sleep peacefully once placed inside?