Toss the cauliflower in a large bowl with 1/3 cup oil and a generous sprinkle of salt and pepper until well coated. Spread out onto 2 rimmed baking sheets. Roast until tender, stirring once or twice, about 30 minutes.
Heat the remaining 2 tablespoons oil in a small skillet over medium-high heat. Add the capers and cook just until they burst and crisp, about 1 minute. Evenly pour over the cauliflower, add the parsley and toss to coat. Season with additional salt and pepper.
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