Ancho chiles are available at specialty-food stores and many supermarkets.
- 2 dried ancho chiles
- 4 cups plus 1 tablespoon vegetable oil
- 1/2 medium onion, cut into 1/4-inch dice
- 2 cloves garlic, minced
- 2 tablespoons dark-brown sugar
- 5 tablespoons ground cumin
- 2 tablespoons dried oregano
- 2 cups dry white wine
- 1 can crushed plum tomatoes (28 ounces)
- 2 cups Homemade Chicken Stock Homemade Chicken Stock, or canned low-sodium chicken broth, skimmed of fat
- 8 Hass avocados
- 1 cup loosely packed fresh cilantro leaves, roughly chopped
- 1/4 cup fresh lime juice
- 3/4 teaspoon salt
- 1/4 teaspoon freshly ground black pepper
- 25 corn tortillas
- 1 1/2 pounds Monterey jack cheese, grated
Place chiles in saucepan; add water to cover. Bring to a boil. Reduce heat; simmer 5 to 10 minutes. Cool slightly, remove stems, and puree chiles and liquid in food processor.
Heat 1 tablespoon oil in a deep skillet over medium heat. Add onions, garlic, brown sugar, cumin, and oregano; saute until onion is soft, 4 to 5 minutes. Add wine, chile puree, tomatoes, and stock; simmer about 20 minutes, until thickened to stew consistency.
Peel, pit, and roughly chop avocados. Toss with cilantro, lime juice, salt, and pepper.
Heat oven to 400 degrees. Heat remaining 4 cups oil in a wide, heavy saucepan over medium heat until very hot but not smoking, 7 to 10 minutes. Using tongs, fry 6 tortillas, one at a time, for 2 to 3 seconds. Drain on paper towel-lined sheet.
Dip fried tortillas in chile sauce to lightly coat both sides. Spoon 2 tablespoons avocado filling on each tortilla; roll up. Spread 1/2 cup chile sauce into large, deep casserole. Arrange rolled tortillas seam-side down in casserole so they fit snugly; repeat entire process, covering bottom of casserole; pour 1 cup sauce over tortillas; sprinkle with half the cheese. Make a second layer using remaining ingredients. Top with remaining sauce and cheese.
Bake enchiladas until heated through, 25 to 30 minutes. Serve immediately.