For the sweet potatoes: Preheat the oven to 350 degrees F.
Toss the sweet potato with olive oil and a sprinkle of salt and pepper on a baking sheet. Roast until tender, about 45 minutes.
For the mashed potatoes: Put the potatoes in a medium pot, cover with cold water and add 2 tablespoons salt. Bring just to a simmer and cook the potatoes, uncovered, until tender, about 45 minutes. Drain.
Peel the potatoes and return them to the pot (if desired, pass them through a ricer or food mill after peeling) and add the sweet potatoes. Mash the potatoes with the milk and butter using a fork or potato masher. Stir in the chopped chipotles, 2 teaspoons salt and freshly ground pepper to taste.
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