Prepare the Cheesecake Filling: In a small bowl, combine the softened cream cheese, 2 tablespoons of granulated sugar, and 1/2 teaspoon of vanilla extract. Mix until smooth and creamy. Spoon small dollops (about 1/2 teaspoon each) of the cheesecake mixture onto a parchment-lined plate or tray and freeze for 20–30 minutes. This makes it easier to handle during assembly.

Make the Cookie Dough: In a mixing bowl, cream together the softened butter, granulated sugar, and brown sugar until light and fluffy (about 2–3 minutes). Add the egg and 1 teaspoon of vanilla extract to the butter mixture, mixing until fully combined. In a separate bowl, whisk together the all-purpose flour, baking powder, and salt. Gradually add the dry ingredients to the wet ingredients, mixing just until a soft dough forms. Do not overmix.

Assemble the Cookies: Preheat your oven to 350°F (175°C) and line a baking sheet with parchment paper. Scoop about 1 1/2 tablespoons of cookie dough and flatten it slightly in your hand. Place a frozen dollop of cheesecake filling in the center and wrap the dough around it, sealing the edges to enclose the filling. Roll the dough into a smooth ball and place it on the prepared baking sheet. Repeat with the remaining dough and filling, spacing the cookies about 2 inches apart.

Bake and Add Topping: Bake the cookies in the preheated oven for 12–15 minutes, or until the edges are lightly golden. Allow them to cool on the baking sheet for 5 minutes before transferring to a wire rack. While the cookies are still slightly warm, combine the cinnamon and sugar for the topping in a small bowl. Roll each cookie gently in the cinnamon sugar mixture to coat.

Serve: Let the cookies cool completely and serve them as a decadent dessert or snack. Store leftovers in an airtight container in the refrigerator for up to 3 days.