Spread squash and chopped carrots on a large baking pan. Pour canola oil all over the carrots and over the squash. Top with salt and pepper. Bake for 40 minutes - but check on the veggies every 10 minutes. You want them to be soft and slightly charred, but not burnt. When done, remove from oven and set aside to cool. When cooled, peel the butternut squash.
Add olive oil to a large dutch oven or soup pot on medium heat. Let olive oil warm and when it shimmers, add diced white onion. Let cook until translucent, about 3 minutes.
Next, add garlic, salt, pepper, curry powder, and cinnamon. Let the garlic cook and spices toast, about 3 minutes, stirring constantly.
Add the vegetable stock to the pot, scraping any onion, garlic, or spices at the bottom of the pot. Add in your carrots and butternut squash into the pot, along with a can of pumpkin. Mix everything well and let cook on medium heat until everything is simmering.
Carefully use an immersion blender to blend everything together. Or, if you don't have an immersion blender, you can use a good blender to bring the soup together.
Once the soup is smooth, serve with pepitas and fresh sage leaves.
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