Cut the bacon crosswise into shorter pieces.
Lay out the bacon pieces flat on a cutting board or parchment paper.
In a small bowl, combine the brown sugar, black pepper, paprika, optional cayenne pepper, and optional crushed red pepper flakes.
Sprinkle the desired amount of seasoned brown sugar over each piece of bacon, spreading it evenly.
Place half of the bacon in a bare, unlined air fryer basket.
Cook at 400°F for 10–12 minutes, flipping halfway through. Be sure to check that the bacon isn’t overcooking, since sugar burns quickly. Cook in 1–2 minute increments as needed to desired crispness.
Once cooked, use tongs to transfer the bacon to a plate—do not use paper towels, or it will stick.
Using a spoon, drizzle your desired amount of maple syrup over each piece. Allow it to sit for 10 minutes to caramelize; it crisps as it cools.
Repeat with the second batch. Reduce cooking time to about 8 minutes, as the preheated air fryer cooks faster.
Optional: sprinkle with fresh cracked black pepper and additional red pepper flakes for color and flavor.