Ingredients
Scale
- 1 pound regular-cut bacon (about 12-16 slices)
- 1 fresh pineapple, cut into 1-inch chunks (or one 20-ounce can pineapple chunks, drained and dried thoroughly)
- ⅓ cup light brown sugar
- Optional: ¼ teaspoon cayenne pepper for a spicy kick
- Optional: 2 jalapeños, sliced into rounds (for spicy variation)
Instructions
- Preheat and prepare: Preheat your oven to 400°F (200°C). Line a rimmed baking sheet with aluminum foil for easy cleanup. If using a wire rack, place it on top of the foil-lined baking sheet and lightly spray with cooking spray.
- Prep the pineapple: If using fresh pineapple, cut off the crown and bottom, then slice away the skin. Remove the core and cut the flesh into 1-inch chunks. You should have about 30-36 pieces. If using canned pineapple, drain thoroughly and pat each piece completely dry with paper towels—this is crucial for crispy bacon!
- Cut the bacon: Using a sharp knife, cut each bacon slice into thirds crosswise. You’ll get three pieces from each slice, which is the perfect length to wrap around a pineapple chunk. If your bacon slices are particularly short, you may need to cut them in half instead of thirds.
- Wrap and secure: Take one piece of bacon and wrap it around a pineapple chunk, slightly overlapping the bacon ends. Secure with a toothpick, pushing it all the way through the bacon and pineapple. The toothpick should go through both layers of bacon to keep everything secure. Place the wrapped bite seam-side down on the prepared baking sheet. Repeat with remaining bacon and pineapple, spacing the bites about ½ inch apart.
- Add the sugar coating: Once all bites are assembled and arranged on the baking sheet, sprinkle the brown sugar evenly over all the bites. Don’t be shy—the sugar creates that amazing caramelized coating! If using cayenne pepper, mix it with the brown sugar before sprinkling.
- Bake: Place the baking sheet in the preheated oven and bake for 20-25 minutes, flipping the bites halfway through (around the 12-minute mark) for even crisping. The bacon should be golden brown and crispy, and the sugar should be caramelized and bubbling. If the bacon isn’t as crispy as you’d like after 25 minutes, turn on the broiler for 1-2 minutes, watching carefully to prevent burning.
- Cool slightly and serve: Remove from the oven and let the bites cool on the pan for 3-5 minutes. This allows the sugar to set slightly and makes them easier to handle. Transfer to a serving platter and serve warm. The bites will be hot inside, so warn your guests!
Notes
- Bacon coverage: Make sure the bacon wraps around the pineapple at least once with a slight overlap. If there are gaps, the pineapple juice can leak out.
- Even cooking: Rotating the pan halfway through baking ensures even browning and crisping.
- Toothpick safety: Soak wooden toothpicks in water for 10-15 minutes before using to prevent them from burning in the oven.
- Crispier bacon: Using a wire rack instead of placing bites directly on the foil allows fat to drip away and creates crispier bacon all around.
- Spicy version: Add a small slice of jalapeño between the bacon and pineapple before wrapping for a sweet-spicy kick.
- Serving temperature: These are best served warm but can be enjoyed at room temperature too.
- Prep Time: 15 minutes
- Cook Time: 25 minutes
- Category: Appetizer
- Method: Baking
- Cuisine: American
- Diet: Gluten Free
Nutrition
- Serving Size: 3 bites
- Calories: 156
- Sugar: 9g
- Sodium: 284mg
- Fat: 10g
- Saturated Fat: 3g
- Unsaturated Fat: 5g
- Trans Fat: 0g
- Carbohydrates: 11g
- Fiber: 0g
- Protein: 6g
- Cholesterol: 18mg