Cain did that for a while we we first got him. He occasionally will still do it because he isn't ready for bed and wants to play when myself an husband are ready for bed haha! We had to ignore Cain the best we could. We made sure he was comfy and had a warm blanket. He got rewarded for going in the kennel. Lots of love when let out. Now if I say time for bed he walks right in and waits for the kennel to be shut. He was easy though!
I'm sure Odin sleeps with you in bed but one thing that always calmed Cain down when we were crate training was Sheba, our blue heeler mix, would go lay right in front of his kennel. It's something she started on her own and Cain wouldn't cry when she was there. And he has always Been around his litter mates so i think he just wanted someone right there! Not sure if you could move his crate closer to your bed so he knows you're not far or so he can see Odin.
I know that Sheba was my life saver when it came to training for us!
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