In a large Dutch oven, heat 2 tablespoons of olive oil over medium heat. Once shimmering, add the ground spicy Italian sausage, breaking it apart with a wooden spoon. Cook for 8-10 minutes until browned and fully cooked, stirring occasionally. When done, transfer the sausage to a plate and set it aside, leaving the delicious drippings in the pot.

In the same pot with the sausage drippings, add the chopped onion and red bell pepper. Sauté them over medium heat for 10-12 minutes until the vegetables are softened and fragrant, stirring frequently. You'll know they're ready when the onion turns translucent and begins to lightly caramelize, enhancing the savory base for your Pumpkin Chili.

Now, stir in the chopped garlic, ground cumin, chili powder, salt, black pepper, and ground cinnamon. Cook this fragrant mixture for about 30 seconds, continuously stirring to bloom the spices and release their wonderful aromas. This step is essential for maximizing flavor in your Cozy Pumpkin Chili.

Carefully add the fire-roasted tomatoes (including juices), drained kidney beans, rinsed black beans, pumpkin puree, chicken broth, and the cooked sausage back into the pot. Mix everything thoroughly until well combined, ensuring the pumpkin puree is evenly distributed. This rich blend forms the heart of your Pumpkin Chili, promising comforting flavors.

Bring the chili to a gentle boil over medium-high heat. Once boiling, reduce the heat to medium-low and cover the pot. Allow it to simmer for about 20 minutes, stirring occasionally to prevent sticking. You'll notice the chili thickening and the flavors melding beautifully as it simmers, creating that ideal comforting texture.

After the simmering time, taste your Pumpkin Chili and adjust the seasoning as needed with additional salt and pepper. If desired, let it rest for a few minutes to enhance the flavors further. Serve the chili hot in bowls, garnished with roasted pumpkin seeds, a dollop of sour cream, shredded cheddar cheese, and sliced avocado.