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1
Adjust oven rack to lower-middle position and heat oven to 300 degrees. Pat beef dry with paper towels and season with salt and pepper. Heat 1 tablespoon oil in large Dutch oven over medium-high heat until just smoking. Cook half of beef, turning occasionally, until well browned all over, about 8 minutes. Transfer to large bowl. Repeat with remaining oil and beef.
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2
Pour off all but 1 tablespoon fat from pot. Add onions and 1/2 teaspoon salt and cook over medium heat until softened, about 8 minutes. Stir in chili powder, cumin, coriander, cayenne, and 1/4 teaspoon pepper and cook until spices darken, about 2 minutes. Add garlic and cook until fragrant, about 30 seconds. Stir in tomato sauce and wine and bring to boil.
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3
Add browned beef, along with any accumulated juices, to pot. Transfer pot to oven and cook, covered, until meat is fork-tender, 2 to 21/2 hours. Transfer beef to large bowl. Strain sauce through fine-mesh strainer, discarding solids, and set aside. (You should have about 2 cups sauce.).
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4
Increase oven temperature to 375 degrees. Spread 3/4 cup sauce over bottom of 13- by 9-inch baking dish; set aside. When beef is cool enough to handle, shred into bite-sized pieces. Add 1 cup cheese and additional 1/4 cup sauce and toss to combine.
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5
Heat tortillas in the microwave for about 1 minute. Arrange warm tortillas on work surface. Place 1/3 cup beef mixture in center of each tortilla. Roll tightly and arrange, seam-side down, in prepared baking dish.
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6
Pour remaining sauce evenly over enchiladas and sprinkle with remaining cheese. Cover with foil and bake until cheese is melted and enchiladas are heated through, 20 to 25 minutes. Serve.
