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Do you have more specifics on the size of his penned in area and the size of his carrier
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As of the size of the fenced off area, I would just make sure there is enough space for him to play and not getting his toy in his waste (in case you have to leave him for a few hours). We got the smallest size of hard carrier for our baby. It is made by Petmates and named "kennel cab" and we got it at Petsmart. You might want to line it with blanket so it's softer for your puppy to sleep on (and easy to clean) and it would also keep him warm.