Preheat your oven to 400°F (200°C). Toss the halved Brussels sprouts with olive oil, salt, and pepper in a mixing bowl until evenly coated.
Spread the coated Brussels sprouts in an even layer on a baking sheet, ensuring they have space around each piece for proper roasting.
Scatter the chopped bacon evenly over the sprouts to allow it to crisp up as they roast.
Roast in the preheated oven for about 20-25 minutes, shaking the pan halfway through to promote even browning. Look for crispy edges and caramelization around the sprouts.
Remove the baking sheet from the oven once the sprouts are tender and some edges are nicely charred, and the bacon is crispy.
Drizzle the maple syrup over the hot roasted Brussels sprouts and bacon, tossing gently to coat everything evenly. The syrup will seep into the leaves, creating a glossy, sweet glaze.
Finish with a sprinkle of freshly ground black pepper or extra salt if desired, then serve immediately for the best flavor and texture.