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Preheat the oven to 425°F (220°C). Arrange the tomato halves cut-side up on a large rimmed baking sheet. Scatter the onion wedges and unpeeled garlic cloves around the tomatoes. Drizzle with 2 tbsp of the olive oil, then sprinkle with the salt, pepper, and sugar.
Roast until the tomatoes are deeply caramelized at the edges, the skins are blistered, and the onion wedges are softened and golden, 40–45 minutes. Remove from the oven and let cool for 5 minutes.
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