Preheat your oven to 350°F (175°C) and line two baking sheets with parchment paper to prevent sticking.

To prepare the dough, combine the butter, softened cream cheese, and vanilla extract in a large mixing bowl. Beat the mixture until it reaches a smooth consistency. Gradually add the all-purpose flour, 5 teaspoons of sugar, baking powder, and 1 teaspoon of ground cinnamon. Mix until the dough is fully combined.

On a floured surface, roll the dough out to a thickness of 1/4 inch. Use a cookie cutter to cut out 48 circles.

Place a teaspoon of apple pie filling on half of the dough circles. Cover these with the remaining circles, ensuring the edges are crimped securely with a fork to seal the filling inside. Arrange the assembled cookies on the prepared baking sheets.

Bake in the preheated oven for 23 to 29 minutes, or until the cookies turn a golden brown color. Allow them to cool for 5 minutes once removed from the oven.

For the topping, mix together 2 tablespoons of sugar and 1 teaspoon of ground cinnamon in a shallow bowl. While the cookies are still warm, roll them in the sugar-cinnamon mixture until evenly coated. Transfer the cookies to a wire rack for a brief cooling period before serving.