In a large Dutch oven, heat 2 tablespoons of olive oil over medium heat. Add 1 pound of ground spicy Italian sausage, breaking it apart with a spatula. Cook for 8-10 minutes until browned and cooked through. Remove sausage and set aside.

In the same pot, add the chopped onion and diced red bell pepper. Sauté for about 10-12 minutes until onion is translucent and bell pepper softens.

Stir in 4 minced garlic cloves, 1 tablespoon of ground cumin, 2 tablespoons of chili powder, 1 teaspoon of kosher salt, ½ teaspoon of ground black pepper, and ½ teaspoon of ground cinnamon. Cook for about 30 seconds to bloom the spices.

Pour in two cans of fire-roasted tomatoes, one can each of drained kidney beans and black beans, and one can of pumpkin puree. Add the cooked sausage back and stir everything until well combined.

Bring the Pumpkin Chili to a gentle boil, then reduce heat to low, cover, and let it simmer for 20 minutes. Stir occasionally.

After 20 minutes, taste and adjust seasoning if necessary. Serve hot in bowls, garnishing with roasted pumpkin seeds, sour cream, cheddar cheese, and avocado.