Wash the potatoes, dry and then spray with olive oil spray. Rub the oil into the potato skin. Place the potatoes and butternut squash into the air fryer, and bake for 45 minutes, or until fork tender.
Let the potatoes and squash cool for about 20 minutes. Slice the potatoes in half. Cut the butternut squash in half. Scoop the seeds out of the squash. Reserve half of the squash for another use.
In a large bowl, add the softened butter. Add the pulp from the half butternut squash to the bowl. Scoop out the potato, leaving about a half inch border in the skin. Add in the milk, crushed red pepper, salt and pepper and using a potato masher, mash the potatoes.
Divide that filling into the potato shells. Top with 1/2 ounce shredded cheese, sprinkle with paprika and broil for 3-4 minutes, or until the cheese is melty and browned. Garnish with chopped cilantro.