01 - Preheat oven to 350°F. Line two baking sheets with parchment paper and set aside.
02 - In a large mixing bowl, beat the softened butter and 1 cup of granulated sugar together using an electric mixer until light and fluffy, approximately 2–3 minutes. Add the egg and vanilla extract, then continue mixing until fully incorporated.
03 - In a separate bowl, whisk together the all-purpose flour, baking powder, and salt. Gradually add the dry mixture to the wet ingredients, mixing on low speed until a soft dough forms. Cover and chill the dough in the refrigerator for 20 minutes.
04 - While the dough chills, combine the softened cream cheese, 1/3 cup granulated sugar, and vanilla extract in a small bowl. Beat until smooth, creamy, and free of lumps.
05 - Roll tablespoon-sized portions of the chilled dough into balls and place them on the prepared baking sheets, spacing about 2 inches apart. Press your thumb or the back of a teaspoon into the center of each ball to create a deep well. Fill each indentation with approximately 1 teaspoon of the cheesecake mixture.
06 - Bake for 11–13 minutes, or until the cookie edges are set and lightly golden. Allow the cookies to rest on the baking sheets for 5 minutes before transferring to a wire rack to cool completely.
07 - Place the caramel candies and heavy cream in a microwave-safe bowl. Heat in 30-second intervals, stirring between each burst, until the caramel is completely melted and smooth.
08 - Drizzle the warm caramel sauce generously over each cooled cookie. Allow the caramel to set at room temperature before serving.