Cut off the top and bottom. Lay the pineapple on its side and slice off the top and bottom of the fruit. This gets rid of the big spiky fronds and creates a stable cutting base.
Trim off the rind. Set the pineapple upright. Work your way around the pineapple, cutting off the rind in strips. Cut deep enough to remove the "eyes," but save as much of the flesh as possible. After you're done, trim off any eyes or bits of rind you may have missed.
Slice the pineapple in half. With the pineapple still upright, slice it straight down the middle into halves.
Slice the pineapple into quarters. Lay each half cut-side down on your cutting board and slice them in half again to make four quarters.
Trim out the core. Lay one quarter on the cutting board like a wedge. Cut into the wedge at an angle to slice out the tough inner core. Repeat with the remaining pineapple. Place on a baking tray or pan in a single layer.
Mix brown sugar, cinnamon, allspice, salt, and chili powder in a small bowl, making sure there are no clumps.
Brush the pineapple wedges with the cinnamon sugar rub, ensuring every inch of the pineapple is covered with the spice mixture.
Prepare your smoker according to the manufacturer's instructions, preheating it to a medium-low temperature (around 225-250℉/107-120℃).
Place the seasoned pineapple wedges directly on the smoker rack in a single layer.
Close the smoker and let the pineapple smoke for approximately about an hour or more until the pineapple is slightly caramelized and infused with smoky flavor, you can flip halfway through, if desired. Check for desired tenderness and doneness.
Remove the smoked pineapple wedges from the smoker and let them cool for 3-5 minutes before serving.
Enjoy with ice cream, sprinkle with coconut flakes, almonds, or balsamic vinegar glaze. Enjoy!