Preheat oven to 300 degrees. Pat beef dry with paper towels and season with salt and pepper.

Heat 1 tablespoon oil in a large Dutch oven. Add half the beef and cook until browned on all sides. Transfer to a plate or bowl. Add remaining vegetable oil and repeat with remaining beef. Remove second batch of beef and place with the previously browned beef. Pour off all but one tablespoon of oil from Dutch oven and add onion plus 1/2 teaspoon salt. Cook for 5 to 7 minutes, stirring occasionally. Stir in jalapeno, chili powder, cumin, coriander, cayenne pepper, and oregano and cook and stir for 1 minute. Add garlic and cook for 1 minute. Stir in tomato sauce and wine, being sure to scrape up any browned bits on the bottom. Return beef and any juices to the Dutch oven and bring to a simmer. Cover and place in oven for 2 to 2 1/2 hours. Transfer beef to a plate. Pour sauce through a fine-mesh strainer. Push on the solids with the back of a spoon to get as much liquid out. Discard the solids. You should have at least 2 cups of sauce. Once meat has cooled some, shred it with 2 forks. Place it in a medium bowl and add 1/4 cup of sauce and 1 cup shredded cheese. Increase oven temperature to 375 degrees.

Grease a 9×13-inch pan. Spread 3/4 cup of sauce in the bottom. Spray the tortillas on both sides with vegetable cooking spray. Bake for 1 minute or until warm and pliable. Place 1/3 cup of beef mixture down the middle of each tortilla. Roll up and place seam side down in the baking dish.

Pour 1 to 1 1/4 cups of sauce over the enchiladas. Sprinkle the remaining cheese on top. Cover with foil (spray the underside with cooking spray so the cheese won’t stick). Bake for 20 to 25 minutes. Serve with cilantro. Cook’s note: Substitute one-half green bell pepper for the jalapeno for less spice.