Preheat your oven to 400°F (200°C) and line a large baking sheet with parchment paper.

Peel, seed, and cube the butternut squash into uniform 1-inch pieces.

In a large mixing bowl, toss the cubed squash with olive oil until evenly coated.

Sprinkle the brown sugar, ground cinnamon, salt, and black pepper over the squash, tossing again to ensure every piece is covered.

Spread the squash in a single layer on the prepared baking sheet, ensuring pieces are not touching.

Roast for 25 to 30 minutes, flipping halfway through, until the squash is fork-tender and the edges are caramelized.