Preparation: Preheat your oven to 350°F (175°C). Line two baking sheets with parchment paper.

Make Cookie Dough: In a large bowl, cream together the softened butter and sugar until light and fluffy, about 2-3 minutes. Add the egg and vanilla extract, mixing until fully combined. In a separate bowl, whisk together the flour, baking powder, and salt. Gradually add the dry ingredients to the wet ingredients, mixing until a soft dough forms.

Make Cheesecake Filling: In a small bowl, beat together the softened cream cheese, sugar, and vanilla extract until smooth.

Shape Cookies: Scoop out tablespoon-sized balls of cookie dough and roll them into balls. Place them on the prepared baking sheets, spacing them 2 inches apart. Use your thumb or the back of a spoon to make an indentation in the center of each cookie.

Fill with Cheesecake: Spoon about 1 teaspoon of the cream cheese mixture into the center of each cookie, filling the indentation.

Add Cherry Topping: Top each cheesecake-filled cookie with a small spoonful of cherry pie filling, making sure to add 1-2 cherries on each cookie.

Bake: Bake for 12-15 minutes, or until the edges of the cookies are lightly golden and the centers are set. Remove from the oven and let cool on the baking sheet for 5 minutes before transferring to a wire rack to cool completely.