Heat a large skillet over medium-high heat. Brown the ground beef with the diced onion until the meat is cooked through and the onion is softened, about 8 minutes. Drain any excess fat.
Stir in the garlic powder, Worcestershire sauce, tomato sauce, paprika, oregano, chili powder, cumin, and black pepper. Let the mixture simmer for 5 minutes until the flavors meld and the sauce thickens slightly.
Meanwhile, heat the oil in a small skillet over medium heat. Working one at a time, dip each tortilla in the hot oil for 10 seconds per side until just softened. Transfer to paper towels to drain. (This step makes the tortillas pliable and prevents them from cracking when rolled.)
Preheat your oven to 350°F. Spread a thin layer of enchilada sauce across the bottom of a 9x13 inch baking dish.
Place a spoonful of the beef mixture down the center of each softened tortilla. Add a pinch of cheese and a few olive slices if using. Roll tightly and place seam-side down in the prepared dish.
Pour the remaining enchilada sauce evenly over the rolled tortillas, then sprinkle with the remaining cheese.
Bake for 20 minutes until the cheese is melted and the edges are bubbling. Let rest for 5 minutes before serving.
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