Preheat oven to 400°. Line a rimmed baking sheet with heavy-duty aluminum foil.
In a large bowl, combine squash, 2 tablespoons olive oil, 1 teaspoon salt, and ½ teaspoon pepper, tossing to coat. Spread squash in an even layer onto prepared pan. Bake for 1 hour.
In a large Dutch oven, heat remaining 2 tablespoons olive oil over medium heat. Add onion, bay leaves, and garlic; cook for 10 minutes, stirring frequently. Add cooked squash and chicken broth. Reduce heat to low; cover, and simmer for 30 minutes. Remove and discard bay leaves. Let cool for 10 minutes.
In the container of a blender, puree squash mixture in batches. Return to Dutch oven over medium- low heat. Add cheese, cream, sour cream, sugar, poultry seasoning, garlic powder, remaining ½ teaspoon pepper, and remaining ¼ teaspoon salt, whisking to combine. Cook for 5 minutes, stirring constantly, until cheese melts. Serve with Seasoned Croutons.
Recipe by Southern Lady Magazine at https://southernladymagazine.com/roasted-squash-soup-recipe/