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Place the dried chiles in a small heatproof bowl and pour the boiling water over them. Let soak for 15 minutes, until the flesh is pliable and the skins have softened. Drain, then scrape the softened flesh from the skins with a spoon and set aside; discard the skins and soaking liquid.
While the chiles soak, heat the oven broiler to high with a rack set 6 inches from the element. Place the tomato halves cut-side up and the garlic head cut-side up on a baking sheet. Drizzle with 1 tbsp of the olive oil. Broil for 10–12 minutes, until the tomatoes are charred at the edges and collapsed and the garlic is golden at the cut surface. Remove from the oven and let cool for 5 minutes, then squeeze the roasted garlic cloves out of their skins directly onto the baking sheet.
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