Preheat the oven to 400°F. Add cubed squash, celery, onion, carrots, sage, thyme, cayenne, and 1/2 teaspoon each kosher salt and black pepper to a large rimmed sheet pan.
40-50 ounces peeled and cubed butternut squash, 4 stalks of celery, 1 medium yellow onion, 4 whole carrots, 10-12 fresh sage leaves, 1/2 teaspoon dried thyme, kosher salt and black pepper, pinch cayenne pepper
Drizzle olive oil on top and toss to coat everything evenly.
3 Tablespoons extra-virgin olive oil
Roast for 40-50 minutes, tossing once midway through if possible. Start to check them periodically near the end of the roasting time. When even the thickest pieces of squash and carrot are tender enough to be pierced easily with a fork, remove from the oven and set aside to cool slightly.
For the smoothest soup: Pour 2 cups of the broth into a large blender and transfer about half of the roasted veggies on top. Blitz on high speed until very smooth, then pour this mixture into a large Dutch oven or stockpot. Repeat with the remaining 2 cups broth and remaining veggies.
4 cups low-sodium chicken or vegetable broth
For fewer dishes: Transfer all of the roasted veggies and herbs directly into a large Dutch oven or stockpot. Pour in all 4 cups of broth and blend with an immersion blender until as smooth as possible.
Simmer on medium heat until ready to serve. Be sure to sample a spoonful and add more salt and pepper to taste. Enjoy!