For wrappers: in a bowl, add the sugar, cream cheese, and vanilla extract and whisk until smooth.
Place a wonton wrapper onto a smooth surface.
Place one tablespoon of cream cheese mixture in the center of each wrapper.
With wet fingers, fold wrappers around the filling and then pinch the edges to seal.
Grease the Air Fryer Basket with cooking spray and then slide inside.
Adjust the temperature of Air Fryer to 350 °F to preheat for 5 minutes.
After preheating, arrange half of the wontons into the greased Air Fryer Basket in a single layer.
Slide the basket into Air Fryer and set the time for 8 minutes.
Meanwhile, for the syrup: in a medium skillet, add water, sugar, cherries, and vanilla extract over medium heat and cook for about 5 minutes, stirring continuously.
Remove from the heat and set aside to cool slightly.
Transfer the mixture into food processor and blend until smooth.
After cooking time is finished, remove the wontons from Air Fryer and place onto a platter.
Repeat with remaining wontons.
Serve the wontons with the topping of cherry syrup.