Preheat your oven to 375°F (190°C). Line a rimmed baking sheet with aluminum foil and place a wire rack on top if available (helps with crisping), or line with parchment paper for easier cleanup.
In a shallow bowl, whisk together the brown sugar, garlic powder, smoked paprika, black pepper, and cayenne pepper (if using). Set aside.
Pat the chicken tenders dry with a paper towel. Wrap one slice of beef bacon spirally around each chicken tender. If the bacon is loose, try tucking the ends under the wrap; beef bacon shrinks tighter than pork, so toothpicks are usually not needed if wrapped snugly.
Press each bacon-wrapped tender into the brown sugar mixture, coating all sides generously. The moisture from the chicken and bacon will help the sugar adhere.
Arrange the tenders on the prepared baking sheet, ensuring they do not touch. Sprinkle any remaining sugar mixture over the tops.
Bake for 20-25 minutes. If the bacon isn't crispy enough, broil for the final 1-2 minutes, watching closely to prevent the sugar from burning.
Remove from the oven when the internal temperature of the chicken reaches 165°F (74°C). Let them rest for 5 minutes before serving to allow the glaze to set.