In a mixing bowl, combine the softened cream cheese, powdered sugar, and vanilla extract. Mix until smooth and creamy.

Lay a tortilla flat on a clean surface. Spoon about 2-3 tablespoons of the cream cheese mixture onto the center of the tortilla, then add 1-2 tablespoons of cherry pie filling on top.

Fold the sides of the tortilla over the filling, then roll it up tightly from the bottom to the top, securing the filling inside. Repeat with the remaining tortillas and filling.

In a large skillet, heat the vegetable oil over medium heat. Once hot, carefully place the chimichangas seam-side down in the oil. Fry for about 2-3 minutes on each side or until golden brown and crispy.

Remove the chimichangas from the oil and place them on a paper towel-lined plate to drain excess oil.

In a small bowl, mix together the ground cinnamon and granulated sugar. While the chimichangas are still warm, sprinkle the cinnamon-sugar mixture over them.

Serve warm with additional cherry pie filling or whipped cream, if desired.