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Preheat the oven to 400°F (205°C). Line a baking sheet with aluminum foil.
Brush the cut sides and cavities of the acorn squash halves with 1 tbsp olive oil, then season with 1/2 tsp salt and 1/4 tsp black pepper. Place cut-side down on the prepared baking sheet and roast for 35–40 minutes, until the flesh is tender when pierced with a fork and the cut edges are golden.
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