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Heat oil in a medium pot over low heat.
Add cauliflower, salt and 1/2 cup water.
Increase heat to medium-low, cover the pot and simmer until cauliflower is tender, about 15 minutes.
Add 4 1/2 cups water and wine, bring to a simmer and cook, uncovered, for 20 minutes or until cauliflower is extremely tender and falling apart.
Purée soup using an immersion or upright blender (working in batches, if necessary) until very smooth and silky.
Transfer soup to a clean pot and let sit for 20 minutes to allow flavors to meld and soup to thicken slightly.
Reheat soup over medium-high heat, stirring occasionally. Serve hot, garnished with a drizzle of oil and a sprinkling of pepper.