Pat the chicken tenders dry with a paper towel. In a small bowl, mix the brown sugar, smoked paprika, garlic powder, salt, black pepper, and cayenne (if using).
Sprinkle about half the seasoning over the chicken tenders and toss to coat.
Wrap each tender in a spiral of bacon, tucking or securing the end with a toothpick. Roll each wrapped tender in the remaining seasoning.
Preheat the air fryer to 380°F (193°C). Place the tenders in a single layer in the basket, seam side down, leaving space between them.
Air fry for 12–15 minutes, flipping halfway through, until the bacon is crispy and the chicken reaches an internal temperature of 165°F (74°C).
Let the tenders rest for 5 minutes. Remove toothpicks and serve warm with your favorite dipping sauce.