Preheat the oven to 400°F (204°C).
Trim the stem ends of the Brussels sprouts and remove any discolored outer leaves. Halve each sprout lengthwise through the stem.
Transfer the prepared sprouts to a large rimmed baking sheet.
Apply olive oil, salt, and pepper. Toss thoroughly to ensure an even lipid and seasoning distribution.
Arrange the sprouts in a single layer, ensuring the flat cut sides are in direct contact with the baking sheet for maximum caramelization.
Roast for 20 to 25 minutes. At the 15-minute mark, check for browning; if necessary, toss to ensure even heat exposure.
Remove from oven when the exterior is charred and the core is tender when pierced with a paring knife.