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Preheat oven to 400 degrees F (200 degrees C).
Place Brussels sprouts in a single layer in a baking dish. Drizzle with olive oil and maple syrup; toss to coat. Sprinkle with bacon; season with salt and black pepper.
Roast in the preheated oven until bacon is crispy and Brussels sprouts are caramelized, 45 minutes, stirring halfway through.