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Start by bringing your oil to medium-low heat in a large pot.
Add in the onion and sauté until the onion is slightly translucent, about 2-3 minutes.
Then, add in the garlic, salt, spices, and fresh tomatoes, and sauté until tomatoes can be easily crushed with a spoon - about another 5-6 minutes.
Then add in the cans of fire-roasted tomatoes, pumpkin purée, vegetable broth, maple syrup, and balsamic vinegar, and stir well.
Simmer soup UNCOVERED for 20 minutes, scraping the bottom of the pan and stirring about every 5 minutes.
When done, remove soup from heat and let cool slightly. Carefully pour the soup into a high-speed blender and blend until completely smooth and creamy, about 1 minute.
Pour the soup back into the pot and keep warm until ready to serve.
Serve soup with any garnishes you like. Grilled bread or grilled cheese sandwiches are a classic pairing.