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In a large skillet over medium heat, heat the olive oil. Add the onion and garlic and sauté until the onion is translucent and aromatic.
Add the ground beef to the pan and sauté until browned and thoroughly cooked. Remove any excess oils from the pan.
Season the cooked ground beef with chili powder, ground cumin, paprika, salt, and black pepper. Mix thoroughly to evenly coat the meat with seasonings.
Pour the tomato sauce and water into the pan and stir to combine. Simmer for about 5 minutes until the sauce thickens and flavors combine. Set aside.
Preheat the oven to 375 degrees Fahrenheit (190 degrees Celsius). Spread shredded cheddar cheese on one-half of a large flour tortilla.
Add a portion of the cooked ground beef on top of the cheese. Sprinkle diced tomatoes, diced bell peppers, black olives, and green onions on top of the beef. Fold the tortilla in half to create a half-moon shape and press to seal the edges. Repeat with remaining tortillas and filling.
Place the filled tortilla pockets on an aluminum foil-lined baking sheet. Bake for 10 to 12 minutes until golden brown and crispy.
Let the baked pockets cool slightly before serving. Garnish with fresh cilantro.
Serve the Loaded Cheesy Pocket Tacos with sour cream, guacamole, and salsa.