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Digging he is "denning" trying to make a comfy spot that is his. Like his ancestors did. At night crying..can he have to potty..I am thinking not as you seem to have it together with going out before bed and once at night already (GOOD JOB) It may be he is just lonely and wants you and hollering...

When dog is lyng down put the treat in front and pull slowly as she begins to crawl or stretch towards it give her the treat continue a few times each day until she does it longer and longer to get the treat keeping food close to her mouth, pulling it away very slowly.