Prepare the pan: Preheat oven to 350°F. Line a rimmed baking sheet with foil, or use a 9x13-inch baking dish for a saucier glaze. Add a wire rack if you want crispier bacon.
Cut the bacon: Slice each bacon strip into thirds. Keep the bacon cold so it’s easier to cut and wrap.
Dry the smokies: Pat the little smokies dry with paper towels so the bacon wraps more securely and the glaze doesn’t turn watery.
Wrap each smokie: Wrap one piece of bacon around each little smokie. Place seam-side down, or secure with toothpicks for easier serving.
Add brown sugar: Sprinkle brown sugar evenly over the wrapped smokies. For extra flavor, mix the sugar with garlic powder, onion powder, cayenne, or chili powder first.
Chill if time allows: Cover and refrigerate for 1 hour to help the sugar settle into the bacon. Skip this step if you’re short on time.
Bake: Bake for 30–40 minutes, until the bacon is browned and the brown sugar is melted and bubbling. Add more time if the bacon still looks pale.
Broil briefly: Broil for 1–3 minutes for extra crisp edges, watching closely so the sugar doesn’t burn.
Rest and serve: Let the Bacon Wrapped Little Smokies rest for 5 minutes, then serve warm with toothpicks or your favorite dipping sauce.