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Preheat oven to 375 degrees F. Wash and dry potatoes, then rub with olive oil and sprinkle with the Kosher salt. Set potatoes on a baking sheet and bake for 1 hour until soft.
Remove from oven and slice potatoes in half lengthwise. Scoop out the insides and transfer them to a large bowl, leaving about 1/8"-1/4" of shell to hold the filling. Arrange shells on the baking sheet.
Add the warm milk, butter, sour cream, cream cheese, and mash with a potato masher. Add half of the cheddar cheese, green onions, garlic powder, salt, and pepper. Stir to combine, then taste and adjust the salt and pepper as needed or add more milk if the potato filling seems too dry.
Fill each shell with the potato filling, then sprinkle with the remaining cheese.
Bake for 15-20 minutes until hot all the way through and the cheese has melted on top.