Prepare the Squash: Preheat the oven to 425°F (220°C). Peel the butternut squash, cut it in half lengthwise, and scoop out the seeds. Cut the flesh into evenly sized 1-inch cubes.
Season the Squash: Place the squash cubes in a large mixing bowl. Add the olive oil, minced garlic, Italian seasoning, paprika, salt, and black pepper. Toss until all the pieces are evenly coated.
Add the Parmesan: Sprinkle the grated Parmesan over the seasoned squash. Toss gently to distribute the cheese across the cubes, reserving a little Parmesan for the final garnish if desired.
Arrange on the Baking Sheet: Line a large baking sheet with parchment paper. Spread the squash cubes in a single layer, leaving space between them. Avoid overcrowding so the edges can caramelize properly.
Roast Until Tender: Place the baking sheet in the preheated oven and roast for 15–18 minutes. Remove the pan and turn the squash pieces with a spatula.
Finish Roasting: Return the squash to the oven and roast for another 15–17 minutes, until fork-tender and golden around the edges. The Parmesan should form lightly crisp spots on the surface.
Add Fresh Herbs: Remove the baking sheet from the oven and let the squash rest for a couple of minutes. Sprinkle with chopped parsley, red pepper flakes if using, and the reserved Parmesan.
Serve Warm: Transfer the roasted squash to a serving dish. Serve immediately while the edges are crisp and the centers are tender.