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Preheat the oven to 400°F (205°C). Place the garlic head cut-side up on a small square of foil, drizzle with 1 tsp olive oil, and wrap tightly. Set on one end of a large baking sheet.
Place the pumpkin halves cut-side down on the same baking sheet. Roast for 40–45 minutes, until the pumpkin flesh is completely tender when pierced with a knife and the cut edges are lightly caramelized, and the garlic cloves are golden and very soft when pressed. Remove from the oven and let cool for 10 minutes.
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