Preheat your oven to 375°F (190°C) and line a baking sheet with parchment paper.

Pat pineapple chunks dry with a paper towel to prevent excess moisture.

In a small mixing bowl, combine brown sugar and cayenne pepper, mixing well.

Wrap each pineapple chunk tightly with a half-slice of bacon, securing with a toothpick if needed.

Roll each wrapped bite in the brown sugar-cayenne mixture to coat.

Arrange bites on the prepared baking sheet with space between them.

Bake for 15-20 minutes, or until bacon is golden brown and crispy.

Allow to cool for a few minutes before serving.