Add cubed butternut squash to a baking sheet and drizzle with oil and a pinch each salt and pepper. Toss to combine.
In the meantime, prepare sauce. Heat large skillet over medium heat. Once hot, add oil and garlic. Cook, stirring frequently, until soft and slightly browned and translucent - about 4-5 minutes.
Remove pan from heat and add tomato sauce, diced chipotle pepper, more adobo sauce (if desired // for more heat), and water (or vegetable broth). Reduce heat to low and return pan to heat. Simmer for 5 minutes, covered (to prevent splattering).
Once bubbling, remove from heat and add roasted butternut squash and 1/4 cup (amount as original recipe is written // adjust if altering batch size) of the enchilada sauce (see photo). Stir to coat. Taste and adjust seasonings as needed. Set aside.
*The best way to cube butternut squash is to start with a large, very sharp knife, cutting off the top and bottom ends. Then cut in half where the small, cylinder shape and round, bulb-shape meet. Use knife to carefully remove skin. Then remove any seeds with spoon or ice cream scoop. Cut into small cubes and proceed with recipe as directed.
*Nutrition information is a rough estimate calculated without additional toppings.
*Recipe inspired by the spaghetti squash tacos in the Smitten Kitchen Cookbook.
*Enchiladas can be frozen individually up to 1 month.