Whisk softened cream cheese, powdered sugar, and vanilla in a bowl.
Whisk until the mixture is completely smooth and uniform.
Spread an even layer of cream cheese onto eight tortillas.
Arrange sliced strawberries in a layer on four tortillas.
Place the remaining four tortillas on top, cream cheese down.
Heat a non-stick skillet over medium heat with 1 tablespoon butter.
Place one or two quesadillas in the hot skillet.
Cook for 2 to 3 minutes on each side.
Cook until tortillas are golden and filling is warm.
Combine the granulated sugar and cinnamon in a small bowl.
Remove the toasted quesadillas from the heat immediately.
Sprinkle the tops with the cinnamon-sugar mixture right away.
Slice each quesadilla into quarters and serve immediately.