Blend Cream Cheese:
In a bowl, stir together cream cheese, vanilla extract, and sugar until smooth and creamy.

Spread on Tortillas:
Smear the cream cheese mixture over the lower part of each tortilla.

Add Cherries:
Spoon approximately 1/4 cup of cherry pie filling onto the cream cheese layer.

Roll and Secure:
Fold in the sides of the tortilla, then roll it tightly, burrito-style. Insert toothpicks to hold the rolls in place.

Prepare Cinnamon Sugar:
Combine ground cinnamon and 1/2 cup sugar in a shallow dish for coating later.

Heat Oil:
Pour 2–3 inches of vegetable oil into a deep pot and heat over medium-high heat.

Deep Fry:
Fry the rolled tortillas 2–3 minutes per side, or until golden brown and crisp.

Drain and Roll in Sugar:
Let the fried chimichangas drain briefly on paper towels, then roll them in the cinnamon-sugar mixture.

Remove Toothpicks and Serve:
Carefully remove the toothpicks before serving. Enjoy warm!