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Preheat the oven to 425°F (220°C). On a large baking sheet, toss the broccoli florets and cherry tomatoes with 2 tbsp of the olive oil, 1/2 tsp salt, and the black pepper until evenly coated. Spread in a single layer and roast for 18ā20 minutes, until the broccoli edges are deeply browned and the tomatoes have softened and begun to collapse.
While the vegetables roast, heat the remaining 1 tbsp olive oil in a 12-inch oven-safe skillet over medium heat until shimmering. Add the garlic and red pepper flakes and cook, stirring frequently, until the garlic is golden at the edges and fragrant, about 2 minutes ā watch closely, as the garlic can brown quickly. Add the balsamic vinegar and rosemary, stir to combine, and cook for 30 seconds until the vinegar reduces slightly and coats the garlic.
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