Prepare the Filling: In a medium bowl, blend the softened cream cheese, 4 teaspoons of sugar, and vanilla extract until creamy. Carefully fold in the cherries from the cherry pie filling.

Assemble the Chimichangas: Spoon an equal portion of the cherry cheesecake filling onto the center of each flour tortilla. Fold in the sides of the tortilla and roll tightly to seal the filling.

Prepare for Frying: Heat vegetable oil in a deep fryer or large pan to 350°F (175°C), ensuring there’s enough oil to fully immerse the chimichangas.

Mix Cinnamon Sugar: In a shallow dish, combine 1 tablespoon of cinnamon with 1/2 cup of sugar. Set aside for coating the chimichangas after frying.

Fry the Chimichangas: Fry the chimichangas in batches, turning occasionally, until they turn golden brown and crispy, approximately 2-3 minutes per side. Remove from the oil and drain on paper towels.

Coat with Cinnamon Sugar: While still warm, roll the fried chimichangas in the cinnamon sugar mixture until evenly coated.

Serve: Serve the cherry cheesecake chimichangas warm, optionally topped with a dollop of whipped cream or a scoop of vanilla ice cream.