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Preheat oven to 425°F. Rub off excess papery skin from garlic heads without separating the cloves. Slice the tips off the heads, exposing the cloves. Place the heads on a piece of foil, drizzle 1 tablespoon oil over each head and wrap into a package. Roast until the garlic feels very soft, 20 to 40 minutes, depending on size. Let cool.
Meanwhile, peel potatoes, if desired, and cut into 2-inch chunks. Place the potatoes and salt in a large heavy saucepan. Add cold water to cover by 2 inches. Bring to a boil. Reduce heat to simmer, cover, and cook until potatoes are very tender, 10 to 15 minutes. Drain well.
Transfer the potatoes to a large bowl. Mash with a potato masher, an electric hand-held mixer or by working through a ricer.
Squeeze the garlic cloves into the potatoes. Add buttermilk and pepper and stir to combine.