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Preheat the oven to 425°F (220°C). Arrange the halved tomatoes cut-side up on a rimmed baking sheet along with the red onion wedges and unpeeled garlic cloves. Drizzle with 2 tbsp of the olive oil and season with the salt and black pepper.
Roast for 30–35 minutes, until the tomatoes are collapsed, deeply caramelized at the edges, and the onion wedges are softened and lightly charred at the tips. Remove from the oven and let cool for 5 minutes, then squeeze the garlic cloves out of their skins and discard the skins.
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