Heat olive oil in a large soup pot or Dutch oven over medium-high heat. Add sausage and cook, stirring occasionally, until the sausage is no longer pink inside, approximately 5 minutes. As the sausage cooks, break it into small pieces with a wooden spoon.
Add the red and Poblano pepper, celery, basil, oregano, rosemary, chili powder, cumin, and cinnamon to the pot. Generously season with salt and black pepper, to taste, and stir to combine. Cook, stirring occasionally, until the veggies have softened, around 5-6 minutes.
Add the chicken stock and simmer for 20 minutes, stirring occasionally.
Add the spinach and cook for another 4-5 minutes, or just until the spinach wilts.
Remove from heat and serve immediately, topped with shredded Cheddar cheese and some additional diced Poblano pepper, if desired.