Rinse and pat dry the asparagus, trimming off the woody ends. Arrange the asparagus on a large plate.
In a small bowl, combine the brown sugar, smoked paprika, and cayenne pepper.
Drizzle olive oil over the asparagus and gently toss to coat. Sprinkle the brown sugar mixture over the asparagus and toss until evenly coated.
Cut each bacon slice in half. Wrap each piece of bacon around an asparagus stalk, ensuring it is tightly secured. Repeat for all asparagus stalks.
Press the wrapped asparagus into any remaining brown sugar mixture on the plate.
Place the bacon-wrapped asparagus in the air fryer basket in a single layer. Air fry at 370°F for 12-15 minutes, or until the bacon is crispy and the asparagus is tender.