- Preheat oven to 425° F.
- In a medium sized bowl, toss cauliflower with olive oil, chili powder, and smoked paprika.
- Spread mixture on baking sheet and place in oven. Place squash halves face down on additional baking sheet and place in oven with cauliflower. Bake for 30-35 minutes until squash is tender and cauliflower nicely roasted and remove from oven.
- In a large stockpot, heat canola oil over medium heat and add red onion and bell pepper, cooking until softened. Add salt, beans, tomatoes, and roasted cauliflower, stirring to combine. Bring mixture to a boil and decrease heat to simmer for 10 minutes. Spoon chili into cooked squash halves and serve with toppings.