Place the butternut squash in large roasting pan with 1 tablespoon olive oil and season chipotle chili powder, cumin, salt and pepper. Cook for 20 minutes, or until the squash has softened and begun to caramelize around the edges.
Remove the squash from the oven and stir in the black beans, chopped cilantro, and 1 cup of the enchilada sauce. Set aside.
To assemble the enchiladas, Dip each tortilla into the remaining enchilada sauce to coat both sides. Spoon 2 Tablespoons of the squash mixture onto the center of each tortilla, top with 1 tablespoon cheese and roll tortilla around filling. Place seam-side down in an ungreased 9 x 13-inch baking dish. Repeat with the remaining tortillas and squash filling.
Pour the remaining sauce over the enchiladas and sprinkle with the remaining cheese.Bake uncovered in the oven for 15 minutes, or until cheese is melted on top and filling is heated through.