Preheat the oven to 325 degrees Fahrenheit.
Add the brown sugar, cumin, and chili powder to a bowl and stir everything together to evenly distribute the seasoning. Set aside.
Slice the bacon in half or into thirds. Note: I recommend cutting the bacon into thirds if using thick cut bacon, which will allow the bacon to wrap around more easily and still become crispy.
Wrap each lil smokie with a section of the sliced bacon.
Secure the end of the bacon into the lil smokie with a toothpick.
Place the prepared bacon wrapped lil smokie into a 9x13 pan.
Repeat with the rest of the bacon, lil smokies, and toothpicks until you have filled the pan.
Sprinkle the seasoned brown sugar over the pan of lil weenies as evenly as you can.
Cook for 1 hour at 325 degrees Fahrenheit.
Depending on your oven, you may need to add 5-7 additional minutes to full melt the brown sugar. However, if you like the crunch of a little brown sugar on top, you can skip this step if the bacon is already fully cooked.
Serve warm and enjoy!