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Heat oven to 425 degrees. Place cauliflower on a rimmed baking sheet and toss with 1/4 cup olive oil and 1/2 teaspoon salt until well coated. Roast for 15 minutes.
In a small bowl, whisk together olives, garlic, lemon juice, 1/8 teaspoon red-pepper flakes and a large pinch of salt. Drizzle in the remaining 1/4 cup olive oil, whisking well.
After the cauliflower has roasted for 15 minutes, add pancetta and cumin seeds to pan and gently mix to combine. Sprinkle Parmesan on top and roast for another 15 to 20 minutes, until cauliflower is tender, the pancetta rendered, and cheese is golden brown and crunchy.
Spoon olive dressing all over roasted cauliflower while still hot and toss to combine. Taste, and add more salt, red-pepper flakes or lemon juice, if needed. Scatter parsley over the top before serving.