01 - Preheat oven to 350°F. Line two baking sheets with parchment paper and set aside.
02 - In a large bowl, use an electric mixer to beat the softened butter and 1 cup of sugar together 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 flour, baking powder, and salt. Gradually add the dry mixture to the wet ingredients, mixing on low speed until just combined. Cover the dough and refrigerate for 20 minutes to firm up.
04 - While the dough chills, beat the softened cream cheese, 1/3 cup of sugar, and 1 teaspoon of vanilla extract in a small bowl until completely smooth and creamy. Set aside.
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 into the center of each ball to create a deep well. Spoon approximately 1 teaspoon of the cheesecake filling into each indentation.
06 - Bake for 11–13 minutes, until the cookie edges are set and lightly golden. Allow the cookies to rest on the baking sheets for 5 minutes, then transfer to a wire cooling rack.
07 - Place the caramel candies and heavy cream in a microwave-safe bowl. Heat in 30-second intervals, stirring between each burst, until the mixture is completely smooth and pourable. Drizzle the warm caramel generously over each cooled cookie. Allow the caramel to set before serving.