Preheat your oven to 400°F (200°C). Line a large baking sheet with parchment paper for easier cleanup, though it's not strictly necessary for crispiness.
In a medium mixing bowl, toss the trimmed and halved Brussels sprouts with olive oil, salt, and pepper. Ensure each sprout is evenly coated.
Spread the Brussels sprouts in a single layer on the prepared baking sheet. Avoid overcrowding the pan, as this will cause them to steam rather than roast and crisp up.
Roast for 20-30 minutes, flipping them halfway through, until they are tender on the inside and deeply browned and crispy on the outside. The exact time will depend on your oven and the size of the sprouts.
While the sprouts are roasting, prepare the balsamic glaze. Pour the balsamic vinegar into a small saucepan. If using honey or maple syrup, add it now. Bring the mixture to a gentle simmer over medium heat.
Continue to simmer for 5-8 minutes, stirring occasionally, until the vinegar has reduced by about half and thickened to a syrupy consistency. Be careful not to let it burn.
Once the Brussels sprouts are roasted to perfection, remove them from the oven. Drizzle the prepared balsamic glaze over the hot sprouts and toss gently to coat.
Serve immediately and enjoy the crispy, flavorful goodness!