Place the walnuts in a dry large skillet over medium heat and toast 3-4 minutes stirring frequently.
Heat the olive oil in a large dutch oven over medium high heat. Add in the onion, garlic, and jalapeños. Cook for 3-4 minutes until soft and fragrant. Stir in the spices and cook 30 seconds.
Pour in the diced tomatoes and tomato sauce along with the broth, and chocolate. Stir until combined.
Add in the squash and toasted walnuts. Bring to a simmer and cover for 1.5 hours. If at the end of the 1/5 hours the soup is too watery simply simmer uncovered for 10 minutes. If it's too thick simply add in some additional water or broth.
Garnish with diced onion, minced cilantro, or sliced jalapeños.
Adapted from my Paleo Pumpkin Chili recipe as well as inspired by the Chocolate Chili recipe in the Nutrition Stripped Cookbook (link above in post)
Nutrition facts are provided as a courtesy, sourced from the USDA Food Database. Net carb count excludes both fiber and sugar alcohols (though the latter are rarely seen on this site), because these do not affect blood sugar in most people. We try to be accurate, but feel free to make your own calculations.