Cook the onion, chili, and spices (salt, pepper, cumin, and cayenne) in the oil until the onion is tender.
Add the garlic and cook for an additional minute, until fragrant.
Add the beef and cook until well-browned. Once browned, add half of the enchilada sauce, the olives, beans, tomatoes, and 1 tbsp. of the cilantro and heat through.
Preheat the oven to 350 degrees.
In another skillet, heat the remaining half of the enchilada sauce over medium-high heat.
One tortilla at a time, drench each tortilla with the sauce (just to make it pliable), shake off excess sauce, lay flat, and fill with 3 tbsp. of the beef and onion mixture in a line down the center. Roll the tortilla up into an enchilada and then place into a baking dish with the crease of the enchilada facing down (so it doesn’t open).
Once the dish is filled with the enchiladas and there is no more space, add the shredded jack cheese, any remaining meat mixture, and the remaining 1 tbsp. of the chopped cilantro to the top.
Cover with foil, and bake in the oven for 15 minutes.
After 15 minutes, carefully remove the foil, and bake 5-10 more minutes until golden-brown and melted.