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Preheat oven to 400°F.
Combine olive oil, balsamic, brown sugar, salt, and pepper in a medium bowl. Add brussels sprouts and toss to coat.
Arrange brussels sprouts on a baking tray. Top with bacon pieces.
Roast in 400°F oven for 25 minutes, then reduce temperature to 350°F for 5-10 more minutes or until until desired tenderness. Check tenderness periodically by piercing centers of the brussels with paring knife.
Serve immediately.