Heat oven to 350°F. Line a large rimmed baking sheet with foil and coat lightly with cooking spray.
In a small bowl, stir together the brown sugar, cayenne pepper, paprika, and black pepper until evenly mixed.
Wrap one piece of bacon around each smokie and secure with a toothpick. Arrange seam side down on the prepared baking sheet.
Sprinkle about half of the brown sugar mixture evenly over the wrapped smokies.
Bake for 15 minutes, then turn each smokie over. Sprinkle the remaining sugar mixture on top.
Return to the oven and bake for another 15 minutes, or until the bacon is crisp and the sugar is caramelized.
Notes
Thin sliced bacon works best for even cooking and crisp results. If using thick cut bacon, lightly cook it first until just flexible before wrapping.
For extra flavor, brush the cooked smokies with barbecue sauce and broil on high for 1 to 2 minutes. Watch closely to prevent burning.
To make these in the air fryer, toss the wrapped smokies in the spiced brown sugar then place them in the air fryer basket. Air fryer at 390°F Air fry for 4 minutes, flip, then cook another 3 - 4 minutes until the bacon is crispy and the sugar has caramelized.
Let the smokies rest for a few minutes before serving. The sugar coating firms up slightly as it cools, making them easier to handle.