Preheat your oven to 325 degrees F. Get out a 9 x 13-inch baking dish and set it aside.
In a small mixing bowl, stir together 1 cup light brown sugar, ½ teaspoon ground cumin, and ¼ teaspoon chili powder. Set aside.
Cut 20 strips regular-cut bacon strips in half crosswise to create 40 short strips of bacon.
Open the 14 ounces little smokies package and drain any excess liquid. Wrap one bacon piece around one smokie. Secure the end of the bacon with a toothpick. Place the sausage in a 9-inch x 13-inch pan with the toothpick sticking up. Repeat with the remaining bacon and little smokies.
Sprinkle the brown sugar mixture all over the little smokies. You want as much as you can get on the sausage, but it's fine if the extra sugar is in the bottom of the pan.
Bake for about 1 hour, until the bacon is cooked through and browned and the sugar has melted into a syrupy glaze. If the sugar isn't completely melted, increase the oven to 350°F and keep baking, checking often so the glaze doesn’t burn.
Transfer to a serving platter and serve warm, leaving the toothpicks in so guests can grab the smokies easily.
Notes
Brown sugar: Dark brown sugar works too and gives a deeper flavor.
Make ahead: Wrap the smokies, cover, and refrigerate overnight. Add the sugar mixture just before baking, and let the dish sit out while the oven preheats.
Double batch: Use a heavy-duty foil-lined half sheet pan. The glaze spreads thinner on the larger pan, so start checking before the hour is up.
Keep warm: Use a slow cooker on WARM (or LOW if your warm runs cool), and keep the smokies at 140°F or above.
Storage: Refrigerate for 3-4 days. Reheat in a 325°F oven to an internal temp of 165°F.