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Preheat the oven to 400°F (205°C). Place the squash halves cut-side up on a large rimmed baking sheet. Drizzle 1 tbsp of the olive oil over the cut surfaces and season with 1/2 tsp salt. Place the garlic head cut-side up alongside the squash and drizzle with the remaining 1 tbsp olive oil. Roast for 40–45 minutes, until the squash flesh is completely tender when pierced with a knife and the cut edges are golden, and the garlic cloves are soft and deeply golden.
Remove the baking sheet from the oven and let the squash and garlic cool for 10 minutes, until cool enough to handle. Scoop the squash flesh away from the skin and set aside. Squeeze the roasted garlic cloves out of their papery skins and set aside with the squash.
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