Some things are worth the effort, things like braised beef rolled into flour tortillas and topped with melted cheese.


  • 2 dried ancho chiles
  • 3 pounds chuck roast, cut in half vertically
  • Kosher salt and freshly ground black pepper
  • 2 tablespoons canola oil
  • 1 onion, chopped
  • 5 cloves garlic, chopped
  • 1 tablespoon ground cumin
  • 3 tablespoons tomato paste
  • 1/2 cup brewed coffee
  • 2 tablespoons apple cider vinegar
  • 2 tablespoons Worcestershire sauce
  • 3 canned chipotle chiles, chopped, along with 1 tablespoon adobo sauce
  • 2 teaspoons dried oregano
  • 1 1/2 cups chicken stock
  • Enchiladas:
  • 12 flour tortillas
  • 2 cups (8 ounces) shredded cheddar cheese
  • 1/4 red onion, diced
  • 1/3 cup chopped cilantro
  • 1 Fresno or red jalapeño chile, sliced
  • 1 jalapeño, sliced


  1. Heat oven to 300 degrees. Adjust rack to center.
  2. Add dried chiles to large heavy-bottomed Dutch oven and cook over medium-high heat, stirring until just darkened with a roasted aroma, about 2 to 3 minutes. Remove chiles and set aside.
  3. Season the beef generously with salt and pepper. Heat oil over medium-high heat, add the meat, and brown on both sides, about 5 minutes per side. Remove beef.
  4. To the same pan, add the onions and garlic, and saute until softened. Stir in cumin and tomato paste and toast for about 1 minute. Stir in coffee, apple cider vinegar, Worcestershire sauce, canned chipotle and adobo, oregano, chicken stock and toasted chiles. Return the beef to the pot. Bring the mixture to a boil, then cover the pot and place in the oven. Braise, covered, for 3 hours, or until tender.
  5. Remove the roast from the pot to a bowl. Allow to cool.
  6. Bring the sauce to a simmer and reduce for 5 minutes. Add the contents from the pot into a food processor, or use a hand-held immersion blender to blend until smooth. You should have roughly 2 cups of sauce for the enchiladas. If not slightly thickened, reduce for longer.
  7. Shred the rested beef, then toss with about 4 tablespoons of the sauce and season with salt. Reserve the remaining sauce for assembling the enchiladas.
  8. Heat the oven to 350 degrees. Grease a 9x13 baking dish.
  9. Ladle a thin layer of sauce to cover the bottom of the baking dish. Lay a tortilla out, fill with beef mixture and sprinkle with a small amount of cheese. Roll up and place seam side down in baking dish. Repeat with remaining tortillas and filling. Pour sauce over the top and top with cheese.
  10. Bake for 25 minutes, until cheese is bubbling and brown. Garnish with chopped cilantro and sliced red and green jalapeños.