Place the bacon on a baking sheet and bake, without turning, for about 10 minutes, until it is about half to three-quarters done. Drain the bacon on a paper towel or wire rack until cool enough to handle then cut each slice into thirds. Wipe off the baking sheet. Leave the oven on.
Meanwhile, whisk the cream cheese in a medium bowl until smooth. Chop the pineapple and mix it in, then mix in the cheddar cheese.
Cut the peppers in half lengthwise and remove any veins and seeds.
Spoon the cream cheese mixture into the pepper halves. Lay a piece of bacon on top of each one and push it down slightly onto the cheese. Generously brush the bacon with barbecue sauce.
Place the stuffed peppers on the baking sheet and bake for 15 to 20 minutes, until the bacon is crispy and the peppers soften slightly. Serve hot.