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Step 1
Preheat your pellet grill to 375°.
Step 2
Core and slice a fresh, ripe pineapple into 1 inch thick rings. Place into your grill and cook for 4-5 minutes per side. We're going for grill marks, bud.
Step 3
Cut the bacon strips in half and lay them out on a parchment-lined baking sheet. Place into the smoker for 10-12 minutes. You want the bacon cooked until the fat starts rendering, but remove before it loses its flexibility.
Step 4
Slice the pineapple rings into bite-sized pieces. Wrap the bacon around the pineapple and secure with toothpicks. Place onto a parchment-lined baking sheet.
Step 5
Cook for 30ish minutes, or until the bacon is fully cooked. Sprinkle the brown sugar onto the tops during the last 10 minutes of cooking.
Step 6
Let cool for 5-10 minutes before serving.