Line two baking sheets with parchment paper and preheat the oven to 350°F (175°C).
In a mixing bowl, beat the softened cream cheese with a hand mixer until smooth and lump-free.
Mix in 1/4 cup of the granulated sugar and the vanilla until fully combined to make the cheesecake filling.
Unroll one pie crust at a time on a lightly floured surface and cut 2-inch circles, re-rolling scraps as needed.
Place half of the crust circles on the prepared baking sheets. Spoon or pipe a small amount of cheesecake filling into the center of each circle.
Moisten the edge of each filled circle with a little water, top with another crust round, and press the edges together using the tines of a fork to seal.
Bake the sealed cookies for 15–20 minutes, until the edges are beginning to turn golden. Remove from oven and let cool until just warm to the touch.
While cookies cool slightly, melt the butter in a microwave-safe dish. In a separate small bowl, combine the remaining 1/2 cup granulated sugar with 1 teaspoon ground cinnamon.
Brush each warm cookie with melted butter, then roll and turn it in the cinnamon-sugar mixture until thoroughly coated. Place on a sheet lined with wax paper to finish cooling.