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Preheat the oven to 425°F / 220°C. Place the cauliflower, red onion, and celery on a large, rimmed sheet pan with 1-2 tablespoons of olive oil, 2 tablespoons of vinegar, and season with salt and pepper. Toss well to coat, then roast for 25 minutes, until everything is slightly charred and starting to soften. Turn the oven down to 400°F / 200°C.
At this point, transfer the roasted vegetables to an oven-safe pan (a 3.5 quart Le Creuset) or continue using the rimmed sheet pan. Add the tomatoes, breaking them up with your hands or using culinary scissors, along with about ½ cup of the reserved juices, the olives, capers, and dates. Stir well and return to the oven for another 40 minutes, or until everything is thick and concentrated.
Once ready, and while still hot, add another tablespoon of vinegar, toss through a handful of herbs and serve alongside good, toasted bread. Finish with a generous drizzle of olive oil.