Reddit mentions of Outward Hound Jigsaw Glider Interactive Doy Toy Puzzle for Dogs

It may just be a matter of finding toys that can keep him engaged. There are toys that are like catnip kickers or static little stuffies, but then there are also some that are battery-operated or plug in (lasers, concealed motion toys, magnetic toys).

My personal preference, especially if I'm not home to supervise are toys that can be active with just the cat's actions alone. This woven straw is one of my cat's favourites because it catches in her claws as she swats it, so as she moves, it follows her motion until it uncatches and flings off, so she'll go chase it.

I've got this cheap little wand that I use to play with her that moves fairly unpredictably and actually got my cat panting because she was so into it.

Another thing I do everyday is spend 15-20 minutes making her chase her meal. I feed wet food during the day and offer a limited amount of kibble at night, so what I do with the kibble is toss it up the stairs or around the house within her sight so she chases each piece to get fed. I do this until she gets so tired that she has to lie down 3 or 4 separate times, and then I let her rest.

After that, I fill some foraging toys with some more kibble so she has something to work for. If your cat is food motivated, this could work well for you too because it keeps them mentally and physically busy. I have a treat ball and a Wobbert (a little more challenging than a regular treat ball) but I find they're quick to solve and not very engaging. Most of the ones I get are dog toys:

• Mad Scientist
  
  
• Jigsaw Slider
  
  
• Flip board level 2
  
  
• Brain mover toy
  
  
• Lucky Slots
  
  
• Training level 3
  
  
• Training level 3
  
  Also, I hide kibble pieces all over her furniture and any cat-friendly furniture. In toys, in any nooks and crannies, in places I want her to explode. It's a good reason to get her feeling like she has a bit of a mission and poking around.

Not sure if this will help you at all, but it's a thought!

My Dory (who was a feral mountain dog for her first two years) isn't typically interested in food-in-bowl unless it's a challenge. Typically she only dives in (and finishes it all as quickly as she can) if:

1. our kitten has been showing interest in her bowl
   
   
2. one of her k9 cousins (including a Husky puppy and a fully grown Golden) is interested in her bowl
   
   
3. we're giving her food in a toy like the Kong Wobbler, Jigsaw Glider or Buster Cube.
   
   This may, or may not, be similar to your dog's apparent hunger for a challenge, or performing a trick, before he eats; you used to make him sit first, now he wants to earn his food through more of a challenge?