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Heat 2 tbsp of the olive oil in a 12-inch skillet over medium-high heat until shimmering. Add the cauliflower florets and diced stems in a single layer and cook undisturbed for 4 minutes, until the undersides are golden brown.
Stir the cauliflower and continue cooking for another 3–4 minutes, stirring occasionally, until the pieces are tender and caramelized on multiple sides. Transfer to a plate and set aside.
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