Prepare the Filling: In a medium bowl, beat the softened cream cheese, 1/4 cup sugar, and vanilla extract until smooth and creamy. Add the chopped strawberries and fold gently until they are uniformly distributed. (Tip: Ensure strawberries are well-drained if using frozen to avoid a watery filling.)
Assemble the Chimichangas: Place 2-3 tablespoons of the cream cheese mixture in the center of each tortilla. Fold the sides of the tortilla inward, then roll it up tightly like a burrito, tucking in the ends to secure the filling.
Prepare for Cooking: Brush the outside of each chimichanga with melted butter if baking, or prepare a skillet with 1-2 inches of vegetable oil heated to 350°F (175°C) if frying.
Cook the Chimichangas: For frying, carefully place the chimichangas seam-side down in the hot oil. Fry until crispy and golden brown, 2 to 3 minutes per side. For baking, place on a parchment-lined baking sheet and bake at 400°F (200°C) for 10-12 minutes, flipping halfway, until crispy.
Coat and Serve: Mix 1/2 cup sugar with 1 tsp cinnamon in a shallow dish. Roll the warm chimichangas in the cinnamon-sugar mixture to coat. Serve immediately with optional toppings like whipped cream, fresh strawberries, or a drizzle of chocolate sauce.