Preheat oven to 350ºF. Prepare a muffin tin and coat with nonstick spray. Fill cups with wonton wrappers. Pressing each carefully into tins leaving an opening in the center.
Place into oven. Bake for 350ºF for 10-12 minutes or until golden brown. Remove from oven. Set aside.
In a medium bowl, combine shrimp, olive oil, garlic and cajun seasoning. Season with kosher salt and ground pepper. Transfer to a skillet.
In a small skillet, heat olive oil and cook shrimp, about 4-5 minutes. Fill each wonton with guacamole and one shrimp. Serve immediately. Garnish with fresh cilantro, if desired.