Pat the beef dry and season it all over with 1 teaspoon salt and ½ teaspoon pepper.
Heat the oil in a large Dutch oven or heavy-bottomed soup pot over medium-high heat. Add the beef in a single layer, cooking in batches if needed, and brown on two sides, about 10 minutes.
Remove the beef from the pot. Leave any oil behind and turn the heat down to medium. Add the jalapeno peppers and garlic. Cook until softened, about 3-4 minutes.
Stir in the pasilla chili powder, ancho chili powder, and New Mexico chili powder and cook, stirring constantly until fragrant.
Add the beef broth, 2 cups water, crushed tomatoes, corn flour, brown sugar, dried oregano, cumin, cinnamon and remaining salt and pepper. Stir well to combine.
Add in the cooked beef and bring to a boil. Reduce to a simmer, cover leaving the lid slightly askew to let some steam escape, and cook for about 2 hours until the beef is very tender.
Taste the chili and adjust the seasoning as necessary. If you prefer it spicier, now’s the time to add more New Mexico chili powder.
Serve hot, garnished with chopped fresh cilantro if desired.
