Heat the olive oil in a large pot or Dutch oven over medium heat. Add the onion and bell pepper, and sauté for 5-6 minutes until softened.
Add the garlic and cook for another minute until fragrant, stirring constantly so it doesn't burn.
Stir in the chili powder, cumin, smoked paprika, and cinnamon. Cook for 1-2 minutes to toast the spices and bring out their flavors.
Add the crushed tomatoes, pumpkin puree, black beans, and vegetable broth. Stir everything together until well combined.
Bring the chili to a boil, then reduce heat to low and let it simmer uncovered for 25-30 minutes, stirring occasionally. This allows the flavors to meld together beautifully.
Season with salt and pepper to taste. If the chili gets too thick, just add a splash more broth.
Serve hot with your favorite toppings. I always go heavy on the cheese and avocado—don't judge!