Prep the pineapple. If using fresh, peel, core, and cut into bite-size chunks about 1 to 1.5 inches wide. Pat them dry with paper towels. If using canned, drain well and pat dry. Dry pineapple helps bacon crisp.

Cut the bacon. Slice thin-cut bacon into thirds or halves so each piece wraps around a single chunk with a slight overlap.

Season, if desired. In a small bowl, mix 1–2 tablespoons brown sugar with 1 teaspoon chili powder or smoked paprika. Lightly toss the bacon pieces or the pineapple in this mixture for a sweet-spicy crust.

Wrap and secure. Wrap each pineapple chunk with a strip of bacon. Overlap the end slightly and secure with a toothpick. Keep the wrap snug, but don’t stretch the bacon too tightly.

Preheat the air fryer. Set to 390–400°F (200°C). Lightly spray or brush the basket with oil to prevent sticking.

Arrange in the basket. Place the wrapped pineapple in a single layer with space between pieces. Don’t overcrowd or the bacon won’t crisp evenly. Cook in batches if needed.

Air fry. Cook for 9–12 minutes, turning once halfway. Start checking at 8 minutes. Bacon should be deep golden and crisp at the edges, and pineapple should look lightly caramelized.

Optional glaze. During the last 2–3 minutes, brush lightly with your honey-maple soy glaze for extra shine and flavor. Avoid heavy glazing, which can cause burning.

Rest briefly. Let the bites sit for 2–3 minutes after cooking. This helps the bacon set and makes them easier to handle.

Garnish and serve. Transfer to a platter, sprinkle with cilantro or green onions, and serve warm. A side of sweet chili sauce or sriracha mayo makes a great dip.