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There is a possibility that it can cause separation anxiety- you need your pup to be okay with being alone from time to time. Does the older dog always sleep in a crate still? Or is that just to see if the puppy responds better? If your older dog always sleeps in a crate, then there isn't much you can do about it, I'm sure they will be fine. However, if you plan on letting the older dog not be confined in the future, it could possibly start issues if the pup isn't ready. The pup could get confused and dislike the change. If you traditionally crate your dogs all the time, no matter what age, it probably won't cause any anxiety since there will be no change even as they age.

I recently did the whole crate training thing a few months ago and made sure to feed my little guy in there every day, every meal. Literally. I put the dish in his crate for meals and let him sleep next to it. It made him associate the crate with his favorite parts of the day. He no longer is fed in his crate, nor does he sleep with the dish, but he now loves to go in 'his house' and relax during the day. I was able to train him to understand the words "in your house" so he knows when it is time to retire for bed. He walks in willingly. If you have not tried that method, give it a go! It definitely made my food motivated beasty love his little hideout cave!
 
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