Tightly wrap one piece of bacon around one little smokie. Place seam down in a glass 13×9 dish. Repeat with remaining little smokies.
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Sprinkle evenly with brown sugar. There should be a thin layer over all the little smokies. Cover and refrigerate for at least 1 hour.
Preheat oven to 350°F. Uncover little smokies and bake for 40-50 minutes. Bacon should be crispy and sugar deeply caramelized.
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