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Preheat oven to 425°. On two large rimmed baking sheets, drizzle squash halves all over with olive oil and season with salt and pepper. Roast until almost tender, 25 to 30 minutes. Let cool slightly, then scoop out squash, leaving a 1/2" border around edges and saving the insides for filling. Reduce oven heat to 350°. In a large skillet over medium heat, heat 1 tablespoon oil. Add onion and cook until soft, 5 minutes. Stir in garlic and cook 30 seconds, then stir in beef, breaking up meat with a wooden spoon. Cook to an internal temperature of 145°. Season with salt, pepper, cumin, and chili powder and cook until no longer pink, 6 minutes. Stir in corn, black beans, enchilada sauce, and reserved butternut squash. Cook until sauce is warmed through. Fill butternut squash boats with beef mixture and top with cherry tomatoes and cheese. Bake until cheese is melty, about 2 minutes. Garnish with cilantro before serving, if using.