Description
This Pineapple Upside Down Sugar Cookies recipe combines the classic flavors of a pineapple upside down cake with the convenience and portability of a cookie. Soft, buttery sugar cookie dough baked atop a luscious caramelized pineapple and cherry topping makes for a delightful dessert or snack perfect for any occasion.
Ingredients
Scale
For the Dough
- 1 cup butter, room temperature
- 1 ½ cups granulated sugar
- 2 eggs
- 2 tsp vanilla extract
- ½ cup sour cream
- 3 cups all-purpose flour
- 1 tsp baking powder
- 1 tsp cornstarch
- ½ tsp salt
For the Topping
- 13 canned pineapple slices
- 13 maraschino cherries
- ½ cup butter, melted
- 1 cup light brown sugar, packed
Instructions
- Prepare the Pan and Topping: Preheat your oven and grease a muffin or cupcake pan. Spoon about 1 tablespoon of the melted butter and brown sugar mixture into the bottom of each cavity, spreading it evenly to cover the base.
- Add Pineapple and Cherries: Place one canned pineapple slice on top of the brown sugar mixture in each cavity. Center a maraschino cherry in the middle of each pineapple slice for a classic look and burst of flavor.
- Make the Dough: In a large bowl, cream the room temperature butter with granulated sugar until light and fluffy. Beat in eggs one at a time, then add vanilla extract and sour cream, mixing well.
- Combine Dry Ingredients: In a separate bowl, whisk together the all-purpose flour, baking powder, cornstarch, and salt. Gradually add the dry ingredients to the wet ingredients, mixing until a soft dough forms.
- Assemble the Cookies: Scoop portions of the dough and gently place them over the pineapple and cherry topping in each cavity, spreading slightly to cover the fruit but not pressing too hard to keep the upside down effect.
- Bake the Cookies: Bake the assembled cookies in the preheated oven until golden around the edges and set in the center, approximately 18–22 minutes.
- Cool and Serve: Allow the cookies to cool in the pan for about 5 minutes. Then carefully invert the pan onto a cooling rack or serving plate so the pineapple and cherry topping are displayed on top. Let cool completely before serving.
Notes
- Make sure the butter for the dough is at room temperature for easier creaming and a smoother dough.
- Using a standard muffin pan helps create perfectly sized cookies with the classic pineapple upside down presentation.
- If canned pineapple slices are too large for your pan, cut them in half.
- Chilling the dough before baking is optional but can help prevent spreading.
- Be careful when inverting the pan to avoid breaking the cookies.
