Preheat your oven to 375 degrees Fahrenheit. Line a baking sheet or a large baking dish with parchment paper.
Prepare the pineapple chunks. If you're using a fresh pineapple, cut out the core and cut 28-30 large chunks (about 1.5 inches in size).
Cut the bacon slices in half. Wrap half a slice of bacon around each piece of pineapple, securing the overlapping ends at the top with a toothpick.
Place the bacon wrapped pineapple on the prepared baking sheet.
In a small prep bowl, whisk together the soy sauce and brown sugar, brushing it on to the bacon and pineapple bites on all sides.
Bake at 375 degrees Fahrenheit for about 20-25 minutes or until the bacon is browned and cooked through and the pineapple pieces have softened but have kept their shape. You can also brush on more of the soy sauce mixture halfway through baking for more flavour (this step is optional).
Serve immediately.
Notes
Make-Ahead Instructions
To make this recipe ahead of time, simply assemble the bacon wrapped pineapple and place it on the baking sheet in the fridge for up to 24 hours in advance. Brush them with the sauce and pop them in the oven when ready to bake and serve.
How to Store Leftovers
Store any leftovers in an airtight container in the fridge and reheat them in the oven or the air fryer until heated through.