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Preheat the oven to 425°F (220°C). Spread the cauliflower florets on a large rimmed baking sheet, drizzle with 2 tbsp of the olive oil, and season with 1/2 tsp salt and 1/4 tsp black pepper. Toss to coat and arrange in a single layer. Roast for 25–30 minutes, flipping once halfway through, until the florets are deeply golden at the edges and tender when pierced with a fork.
While the cauliflower roasts, heat the remaining 1 tbsp olive oil in a large pot or Dutch oven over medium-high heat until shimmering. Add the sliced cremini mushrooms in a single layer and cook undisturbed for 4–5 minutes, until browned on the underside, then stir and cook for another 2–3 minutes until the mushrooms are golden and any released liquid has evaporated. Transfer the mushrooms to a plate and set aside.
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