[Bobby dog]

Have you had a dental exam for your dog? Kind of sounds like he might have trouble with harder foods.

Hard food does not keep teeth clean and wet food does not harm teeth. Wet food is a healthy addition to a kibble diet. Brushing his teeth several times a week is one of the best ways to care for his teeth.
Here’s some info on feeding canned foods and dental care.
/choosing-dog-food/canned-or-dry-dog-food/
/choosing-dog-food/dry-dog-food-cleaner-teeth/