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Preheat the oven to 400°F and line a large baking sheet with parchment paper.
Place the squash cubes on the prepared baking sheet and toss with olive oil, maple syrup, cinnamon, salt and pepper. Spread the squash into a single layer to avoid them overlapping.
Roast until the edges are golden brown and begin to caramelize, about 30 to 35 minutes, tossing halfway through. Transfer to a serving dish and garnish with rosemary.