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Preheat the oven to 425°F (220°C). Spread the eggplant cubes on a large rimmed baking sheet, drizzle with 3 tbsp of the olive oil, and season with 1/2 tsp of the salt and 1/4 tsp of the pepper. Toss to coat, then spread in a single layer.
Roast the eggplant for 20 minutes, until the undersides are golden and beginning to caramelize. Scatter the cherry tomatoes over the pan, season with the remaining 1/4 tsp salt and 1/4 tsp pepper, and return to the oven for 12–15 minutes more, until the tomatoes have burst and the eggplant is deeply browned and tender throughout.
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