Heat olive oil in a large Dutch oven over medium heat. Add Italian sausage and cook for 8-10 minutes, breaking into bite-sized pieces, until browned and cooked through.

Use a slotted spoon to remove sausage and set aside on a paper towel-lined plate. Keep about 1 tablespoon of rendered fat in pot.

Add chopped onion and bell pepper to the same pot. Cook for 10-12 minutes until softened and onion becomes translucent.

Stir in garlic, cumin, chili powder, salt, black pepper, and cinnamon. Cook for 30 seconds to bloom the spices.

Add tomatoes, kidney beans, black beans, pumpkin puree, chicken broth, and browned sausage. Stir until completely combined.

Bring to a boil over medium-high heat, then reduce to medium-low, cover, and simmer for 20 minutes, stirring every 5 minutes.

Taste and adjust salt and pepper as needed. Serve hot with desired garnishes.