Pat the beef dry and season it all over with 1 teaspoon salt and ½ teaspoon pepper.
3-4 pounds boneless beef chuck roast, 3 teaspoons kosher salt, 1 teaspoon ground black 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.
2 tablespoons vegetable oil
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.
3 jalapeno peppers, 8 cloves garlic
Stir in the pasilla chili powder, ancho chili powder, new mexico chili powder and cook, stirring constantly until fragrant.
2 tablespoons ground pasilla chili powder, 2 tablespoons dried ancho chili powder, 1-2 teaspoons dried New Mexico chili powder
Add the beef broth, 2 cups water, crushed tomatoes, corn flour, brown sugar, dried oregano, cumin, cinnamon and remaining salt and pepper.
2 cups low-sodium beef broth, 2-2½ cups water, 1 cup canned crushed tomatoes, 2 tablespoons corn flour, 1 tablespoon brown sugar, 2 teaspoons dried oregano, 2 teaspoons ground cumin, ½ teaspoon ground cinnamon
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.
Chopped fresh cilantro