Preheat the oven to 400°F and line a sheet pan with a cooling rack.
Trim off the woody ends of the asparagus, about 1 1/2 to 2 inches of the bottoms. Place the asparagus in a large mixing bowl and toss them with the olive oil, garlic powder, onion powder, salt, and pepper.
Wrap a strip of bacon around 3 pieces of asparagus. Place the wrapped asparagus on the cooling rack with the seam side down. Repeat this process with all the remaining bacon and asparagus. Sprinkle the brown sugar over the bacon.
Bake for 30 to 40 minutes until the bacon is crispy.
Notes
Trim the ends of the asparagus so they are tender and easy to eat
Use a cooling rack for the crispiest bacon
Place seam side down so the bacon stays wrapped while cooking
Flip halfway through if not using a rack
Sprinkle brown sugar evenly so it melts over the bacon