In a bowl, beat cream cheese, powdered sugar, and vanilla extract until smooth and creamy.
Gently fold in the cherry pie filling, being careful not to break up the cherries too much.
Spoon a generous amount of the filling mixture onto the lower third of each tortilla.
Roll up the tortillas tightly, folding in the sides to seal the filling inside.
Brush each chimichanga with melted butter, then lightly spray with cooking spray or brush with oil.
Preheat air fryer to 375°F (190°C). Arrange chimichangas seam-side down in the basket, making sure they don’t touch.
Cook for 6–8 minutes, flipping halfway through, until golden and crispy. Alternatively, deep fry in hot oil (350°F/175°C) for 2–3 minutes until crispy and golden. Drain on paper towels.
While still warm, mix granulated sugar and cinnamon in a shallow dish. Roll each chimichanga in the cinnamon-sugar mixture until fully coated.
Serve warm, optionally with whipped cream or a drizzle of chocolate sauce.
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