Adjust oven rack to lower middle position and heat oven to 325° F
In large Dutch Oven over medium heat toast the ancho chilis for 5-6 minutes. once done move to plate and set aside.
Pat beef cubes dry with paper towel and season with salt and pepper to taste.
Heat 1 tablespoon oil in empty dutch oven, over medium heat until just smoking. Brown half of the meat on all sides, 7-10 minutes. Transfer to plate and continue with the other half of the meat.
Add onions and ¼ teaspoon salt to the fat that is left in the pan, cook until softend about 5-6 minutes. Stir in garlic, jalapeno, oregano, cumin and cinnamon and cook until fragrant. about 30 seconds more.
Stir in the flour and cook for 1-2 minutes to cook out the flour taste, stiring with the onions and other ingredients.
Slowly whisk in the beef broth, scraping up any browned bits on the bottom. Add in the tomatoes, and their juices and add the toasted ancho chilies and bring to a simmer.
Add in the beef and all the juices from the plate, cover and transfer to the oven, cook for 1 hour.
Add in potatoes and bell peppers, cover and continue cooking for another 1-1½ hours longer, until beef and potatoes are tender.
Remove pot from oven and discard the ancho chilies, stir in the olives and let sit until they are heated through, about 3-5 minutes. Add in cilantro and season with salt and pepper.