Take a sheet pan and cover it with aluminum foil (this will help keep the drippings from sticking to the pan). Place a wire baking rack in the sheet pan on top of the aluminum foil. Set aside.

Remove the bacon from its packaging and cut in half using kitchen shears or a sharp knife and cutting board. Set aside.

Drain the pineapple (if using canned), and set on a paper towel-lined plate to soak up excess juice. Set aside.

Measure out the brown sugar and pour it into a small bowl with a flat bottom. If using smoked paprika, measure it out and pour it in the same bowl, stirring to thoroughly mix.

Take one piece of bacon and lay it out on the rack. Place one pineapple chunk at one end of the bacon strip, then use your hands to roll the bacon around the pineapple in a straight line until the pineapple chunk is enveloped by the bacon.

Take the bacon-wrapped pineapple and carefully roll it around in the brown sugar mixture until all sides are covered. Make sure the bacon doesn’t become unrolled when doing so.

Place the sugar-coated bacon-wrapped pineapple onto the sheet pan rack. Make sure to place it with the end of the bacon strip on the bottom so it doesn’t come undone.

Repeat the process with the other pieces of bacon and pineapple, making sure to space the wrapped pieces on the rack so none are touching.

Place in a cold oven and set the temperature to 400°F. Set the timer for 20 minutes. Once the timer goes off, turn the sheet pan 180 degrees (so the back of the pan is now facing the front of the oven) and set the time for another 20 minutes.

Check the bacon bites to see if the bacon is starting to brown and get crispy. If not, put them back in the oven for another 5 minutes. At this point they should be brown. If they’re still not brown or crispy enough for you, turn the oven to broil (on low heat) and broil them for 1-2 minutes max. Check them after the first minute to make sure they don’t burn as it will happen quickly.

Once cooked, take the pan out of the oven and carefully remove the bites from the rack with a set of tongs, making sure not to pull the bacon apart. Serve when hot!