Preheat the oven to 350°F (175°C).
Lightly coat a miniature muffin pan with cooking spray to prevent sticking.
Gently press each wonton wrapper into the muffin pan cavities to form small cups, ensuring edges are slightly flared.
Bake the wonton wrappers for 5 minutes until lightly golden and crisp. Remove from oven, let cool slightly, and carefully remove cups from the pan.
In a skillet over medium heat, cook the sausage, breaking it into crumbles, until fully cooked (about 8-10 minutes). Drain excess fat.
In a medium bowl, combine cooked sausage, Monterey Jack cheese, Cheddar cheese, black olives, and ranch dressing. Stir until well blended.
Spoon the sausage mixture into each baked wonton cup, filling generously but not overflowing.
Place filled wonton cups on a baking sheet or back into the muffin pan. Bake for 10-15 minutes until the filling is bubbly and slightly browned.
Remove from oven and let cool for 2-3 minutes. Garnish with fresh parsley or chives, if desired, and serve.