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Preheat the oven to 425°F (220°C). Working in batches, pulse the cauliflower florets in a food processor (or grate on the large holes of a box grater) until broken down into rice-sized pieces. Spread the cauliflower rice on one half of a large sheet pan, toss with 2 tbsp olive oil, 1/2 tsp salt, and 1/4 tsp black pepper, and spread into an even layer.
Toss the cherry tomatoes on the other half of the sheet pan with 1 tbsp olive oil and 1/4 tsp salt. Transfer the pan to the oven and roast for 20–22 minutes, until the cauliflower rice is lightly golden at the edges and the tomatoes are blistered and beginning to burst.
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