Sprinkle 2 tablespoons of sugar over the strawberries. Stir to evenly coat. Set aside.
Combine the remaining sugar and cinnamon in a small bowl. Set aside.
In a small bowl, mix the cream cheese, vanilla, and 1/2 cup of confectioners’ sugar together until smooth and creamy.
Preheat the oven to 425°F. Divide the filling between the tortillas, covering half the surface. Fold in half and press down gently but firmly. Arrange the quesadillas on a large baking sheet.
Bake for 4 minutes. Flip the quesadillas and gently press down with a spatula. Bake for a further 4 minutes or until they are a very light golden brown.
Remove from oven and immediately brush with melted butter then sprinkle the quesadillas with the cinnamon sugar mixture.
Using a hand mixer or a stand mixer fitted with a whisk attachment, beat the heavy cream and remaining confectioners’ sugar on medium-high speed until soft peaks form, about 3 minutes.
Arrange quesadillas on a serving plate and layer with strawberries and whipped cream. Serve immediately.