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Step 1
Preheat the oven to 400 degrees F. Scrub the potatoes well, dray, and pierce each potato several times with a fork.
Step 2
Place each potato on a sheet of aluminum foil. Drizzle each potato with olive oil and sprinkle with 1/2 teaspoon salt. Roll the potatoes to coat the skin with the salt and oil and then wrap them in the foil. Place the wrapped potatoes onto a baking sheet and bake at 400 degrees F, until potatoes are fork-tender for 40-45 minutes.
Step 3
Once potatoes have been baked, allow them to cool for 5-10 minutes. Slice the potatoes in half and then using a spoon, melon baller, or cookie scoop, scoop out the flesh of the potato into a large mixing bowl, leaving behind a 1/4 to 1/2-inch border around the potato skins.
Step 4
Place the butter and milk into a heat-safe container and microwave in 30-second intervals until the butter is melted and the milk is lukewarm.
Step 5
Mash the potato flesh well with a fork. Add the warm butter, milk, and salt to the potatoes and mix well to incorporate. Stir in sour cream and 1/4 cup of the shredded cheese into the potato filling.
Step 6
Place half the potato skins onto a baking sheet and season with salt and pepper. Generously fill the stuffing into the potato skins and top with the remaining cheddar cheese.
Step 7
Return the potatoes back to the oven and bake for 15 minutes, until the cheese is melted and the filling is warmed through. Serve immediately.