Lay the pineapple on its side and cut off the bottom with a sharp knife. I keep the top, so I have something to hold onto while peeling it.
Set the pineapple upright, and working your way around the pineapple, slice off the rind in strips. Cut deep enough to remove the eyes without removing too much of the flesh. Trim off any bits of rind or eyes that are still there. Then, cut off the top.
Stand the pineapple upright, and cut it in half lengthwise. Then slice each half into quarters, and slice them in half again to make four quarters for a total of eight wedges.
Trim off the tough inner core from each wedge at an angle. (I save the cores for pineapple juice because they have more flavor than the flesh.) Place the wedges on a tray in a single layer.
Mix the brown sugar, cinnamon, allspice, chili powder, and salt in a small bowl, making sure there are no clumps. Then sprinkle the spice mixture onto the pineapple wedges, covering every inch of the pineapple.
Preheat the smoker according to the manufacturer's instructions to 225-250℉ (107-120℃) or around medium-low.
Place the pineapple wedges directly on the smoker rack in a single layer. You may want to put a tray underneath to catch any juice that drips out.
Close the smoker and smoke the pineapple for approximately an hour, or until the pineapple is lightly caramelized and infused with smokiness. Flip halfway through if desired (not necessary).
As soon as the pineapple reaches the desired tenderness and doneness, remove it from the smoker and let it cool for 3-5 minutes before serving. Enjoy!