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Place the milk in a small saucepan to warm over low heat.
Heat the olive oil in a large, heavy pot or Dutch oven and toast the pepper flakes over medium heat, if using. Add the onion and garlic and cook until soft and translucent.
Increase the heat to medium-high and add the tomatoes. Cook until fragrant and softened, then add the cauliflower. Cook without stirring for a couple minutes, then stir to let it brown on another side. Cook for about 4 minutes, or until the cauliflower is dark in spots and golden in others.
Reduce the heat to low and let the pan cool down a bit, then add the hot milk and salt, stir, and cover. Cook until the cauliflower is tender, about 7 minutes. Taste and season with more salt as needed.