Peel and dice winter squash into ¾ inch cubes. Place on a parchment lined sheet pan and drizzle with oil, generous salt and pepper, Stir and roast in the hot oven for 15 minutes, and feel free to broil for just a minute or two to get them crispy.
Make the QUICK Mole Sauce: Place all the ingredients ( EXCEPT CHOCOLATE and TAHINI PASTE) in a blender. Blend until smooth. Place this Mole sauce in a small pot, bring to a simmer over medium heat, cover ( it will splatter) and cook 7-8 minutes over medium low heat. Stir in tahini sauce and chocolate until melted and combined. Taste, adjust salt and sweetness, adding a teaspoon of maple if necessary (some chocolate is sweeter than others). Turn heat off and set aside.
In a 9 x 13 greased baking dish, brush ⅓ of the quick mole sauce on the bottom.
Warm the tortillas (place in the oven, fry in a skillet, microwave, grill over a gas flame) to make them soft and pliable, then stack them (frying gives them the best texture).
Gather your ingredients…crumbled queso (or jack cheese) drained rinsed black beans, roasted squash and begin assembling the enchiladas.
Fill each tortilla with 2-3 tablespoons crumbled queso, ¼ cup roasted squash and ⅛ cup black beans. Roll and place seam side down in the baking dish over the mole sauce.When you have filled the baking dish, brush a generous amount of mole sauce all over the top of the enchiladas, saving any extra for touching up later.
Cover with foil and bake at 375F for 20-25 minutes. Uncover, and bake for 5-10 more minutes, adding extra mole sauce, if necessary. Pull from oven, sprinkle with more crumbled queso (if you want) toasted sesame seeds, avocado, pumpkin seeds and fresh cilantro and serve with a dollop of sour cream.
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