Preheat the oven to 350°F (175°C). Line two baking sheets with parchment paper to prevent sticking and ensure even baking.
Make the Cheesecake Filling
Using a hand mixer, beat the cream cheese in a mixing bowl until smooth and lump-free. Add ¼ cup of granulated sugar and the vanilla extract, and mix until fully incorporated.
Prepare the Pie Crust
Roll out the pie crusts onto a clean surface. Using a 2-inch round cutter, cut circles from the dough. Re-roll the scraps to maximize the number of circles.
Assemble the Cookies
Place half of the dough circles onto the prepared baking sheets. Spoon or pipe a small amount of the cheesecake filling onto the center of each circle. Wet the edges of the dough lightly with water, then place the remaining dough circles over the filling. Seal the edges by pressing gently with the tines of a fork.
Bake the Cookies
Bake the assembled cookies in the preheated oven for 15–20 minutes, or until the edges are lightly golden. Allow the cookies to cool on the baking sheet for 5–10 minutes until they are safe to handle.
Prepare the Cinnamon-Sugar Coating
Melt the butter in a microwave-safe dish. In a separate shallow bowl, combine the remaining ½ cup granulated sugar with the ground cinnamon.
Coat the Cookies
While the cookies are still warm, brush each one with melted butter. Roll them in the cinnamon-sugar mixture until fully coated. Transfer to a cooling rack or wax-paper-lined tray to cool completely.
Notes
To make this recipe gluten-free, substitute the regular pie crust with a gluten-free pie crust. Additionally, confirm that your cinnamon and other ingredients are certified gluten-free to avoid cross-contamination.