Ingredients

• 1 butternut squash, halved and seeded
• 2 ounce crushed tomatoes
• 4 cup broccoli florets, florets
• 4 cup vegetable broth
• 1 yellow onion, diced
• 4 clove garlic, minced
• 2 tablespoon olive oil
• 1 teaspoon dried thyme
• 1 teaspoon smoked paprika
• salt and black pepper
• 0.5 cup heavy cream
• 1 cup sharp cheddar cheese, shredded
• 3 slice crusty bread, cubed
• 2 tablespoon unsalted butter
• 0.25 cup sharp cheddar cheese (croutons), grated
• 2 clove garlic (croutons), minced
• 2 tablespoon fresh basil, chopped

Steps

1. Preheat oven to 400°F (200°C). Line two large baking sheets with parchment paper.
2. Place butternut squash halves cut-side down on one prepared baking sheet. Brush the skin lightly with 1 tablespoon of olive oil. Roast in preheated oven for 35-40 minutes until the flesh is very tender and lightly caramelized at the edges.
3. While squash roasts, prepare crouton ingredients: Cut bread into small 1-inch cubes. Heat 2 tablespoons butter in a medium saucepan over medium-low heat. Add 2 minced cloves garlic and cook for 1 minute until fragrant.
4. Add bread cubes to the butter-garlic mixture, tossing to coat evenly. Spread on the second baking sheet in a single layer. Sprinkle with 1/4 cup grated cheddar cheese, salt, and pepper.
5. When butternut squash has about 10 minutes left, place the croutons in the oven on a separate rack. Bake for 8-10 minutes, stirring halfway through, until golden and crispy.
6. Remove squash from oven and set aside to cool slightly. Scoop the soft flesh away from the skin and set aside. Remove croutons and transfer to a paper towel to cool.
7. Heat 1 tablespoon olive oil in a large heavy-bottomed pot or Dutch oven over medium heat. Add diced onion and sauté for 5-6 minutes until softened and translucent.
8. Add 4 minced cloves garlic, 1 teaspoon dried thyme, and 1 teaspoon smoked paprika to the pot. Stir constantly for 1 minute to bloom the spices.
9. Pour in 2 cans (28 oz each) crushed tomatoes and 4 cups vegetable broth. Add the roasted butternut squash flesh. Stir well to combine.
10. Bring the soup to a gentle simmer over medium-high heat, then reduce heat to medium-low. Simmer for 10 minutes to allow flavors to meld.
11. While soup simmers, add 4 cups fresh broccoli florets to a separate pot of lightly salted boiling water. Blanch for 3-4 minutes until tender-crisp, then drain well.
12. Using an immersion blender, carefully blend the soup until completely smooth and velvety. Work in batches if necessary, or use a fine-mesh strainer to press the mixture through after blending.
13. Stir in the blanched broccoli florets. Season with salt and black pepper to taste. Reduce heat to low and stir in 1/2 cup heavy cream until fully incorporated.
14. Remove from heat. Add 1 cup shredded sharp cheddar cheese, stirring until completely melted and the soup is creamy and smooth.
15. Ladle soup into warm bowls. Top each serving with a handful of warm cheddar croutons and a pinch of fresh chopped basil. Serve immediately while hot.