Place squash halves in a microwave-safe bowl and cover bowl with plastic wrap. Cook in microwave until flesh is very tender, 12 to 15 minutes.
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Pour about 1 inch of oil in a skillet and place over medium-low heat. Fry tortillas in oil until softened and lightly browned, about 10 seconds per side. Drain tortillas on paper towel-lined plates.
Preheat oven to 325 degrees F (165 degrees C).
Spread a thin layer of enchilada sauce into the bottom of a 9x13-inch baking dish.
Sprinkle cinnamon, garlic salt, and black pepper over squash; mash until smooth. Stir black beans and cilantro into squash mixture until filling is well mixed.
Place a tortilla in the bottom of the baking dish; spoon filling down the middle and roll tortilla around filling, keeping it seam-side down. Repeat with remaining tortillas and filling. Stack rolled tortillas on top of each other, if needed. Pour remaining enchilada sauce over tortillas and top with Colby-Jack cheese.
Bake in the preheated oven until cheese is melted, 25 to 30 minutes.
Aluminum foil helps keep food moist, ensures it cooks evenly, keeps leftovers fresh, and makes clean-up easy.
383.73 calories; 13.87 g protein; 58.89 g carbohydrates; 10.65 g dietary-fiber; 4.99 g sugars; 12.46 g fat; 5.87 g saturated-fat; 21.77 mg cholesterol; 18810.61 IU vitamin-a-iu; 5.64 mg niacin-equivalents; 0.6 mg vitamin-b6; 46.72 mg vitamin-c; 82.28 mcg folate; 172.22 mg calcium; 3.96 mg iron; 131.22 mg magnesium; 1185.47 mg potassium; 829.81 mg sodium; 0.28 mg thiamin; 112.1 calories-from-fat; 58 percent-of-calories-from-carbs; 27 percent-of-calories-from-fat; 13 percent-of-calories-from-protein; 13 percent-of-calories-from-sat-fat