Pre-heat the oven to 375. Lightly mist 12 cups in a standard muffin/cupcake tin with cooking spray and set aside.
Place the sausage in a medium skillet and bring to medium heat. Cook, breaking up with a wooden spoon into smaller pieces, until sausage is cooked through. *If using a vegetable that needs to be cooked (mushrooms, peppers, etc)*, add those to the sausage and continue to cook for a few minutes until the vegetables are softened. If you’re using pineapple you don’t need to cook it, you can just add it in the next step.
Transfer the cooked sausage and the cooked vegetables or chopped pineapple to a mixing bowl. Add most of the chopped pepperoni (reserve some to sprinkle on top), the pizza sauce and the Italian seasoning and stir together to combine.
Push a wonton wrapper into the bottom of each of the sprayed cups in the muffin tin. Using about half of the sausage mixture, spoon evenly into the wonton wrappers. Sprinkle about half of the shredded mozzarella evenly over the top of each cup. Press another wonton wrapper on top and repeat the layering steps with the remaining sausage mixture and shredded mozzarella. Sprinkle the reserved pepperoni on top of the completed cups.
Bake for 18-20 minutes until the wontons are golden brown and the contents are heated through. Remove the muffin tin from the oven and allow to cool for 2-3 minutes before removing from the tin.