Preheat oven to 375 degrees F (190 degrees C). Line 2 baking sheets with parchment paper.
Arrange butternut squash slices in a single layer on each baking sheet. Drizzle 1 tablespoon of olive oil over each layer; season each with 1 teaspoon Italian seasoning, salt, and pepper.
Bake in the preheated oven until squash is soft but still firm to the bite, about 15 minutes.
Heat a large skillet over medium heat; cook and stir beef and garlic until browned, about 5 minutes. Drain grease. Mix in remaining 1 teaspoon Italian seasoning, pasta sauce, brown sugar, basil, and 1 1/2 teaspoon salt. Simmer, stirring occasionally, until flavors combine, about 10 minutes.
Mix remaining 1 teaspoon salt, ricotta cheese, eggs, 1/2 cup Parmesan cheese, and parsley together in a bowl.
Layer 1/3 of the squash slices in the bottom of a 9x13-inch baking dish. Cover squash with 1/2 of the ricotta mixture, 1/2 of the mozzarella cheese and 1/3 of the beef mixture. Repeat layers, ending with remaining squash slices and sauce. Sprinkle 2 tablespoons Parmesan cheese on top.
Bake in the preheated oven until cheeses are melted and sauce is bubbly, about 30 minutes. Let stand for 10 minutes before serving.
Nutritional Facts
Per 10 servings
Calories: 443
Carbohydrate: 41g
Fat: 21g
Fiber: 6g
Protein: 25g
Sugar: 15g
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