Description
These Pineapple Upside Down Sugar Cookies bring a delightful twist to a classic dessert by combining the tropical sweetness of pineapple and cherries with soft, buttery sugar cookie dough. Topped with a caramelized brown sugar glaze, these individual cookies are baked to golden perfection and inverted to showcase their glossy fruit topping, making them a festive and flavorful treat perfect for any occasion.
Ingredients
Cookie Dough
- 1 cup unsalted butter, at room temperature
- 1 1/2 cups granulated sugar
- 2 large eggs
- 2 teaspoons vanilla extract
- 1/2 cup sour cream
- 3 cups all-purpose flour
- 1 teaspoon baking powder
- 1 teaspoon cornstarch
- 1/2 teaspoon salt
Topping
- 13 canned pineapple slices, drained
- 13 maraschino cherries
- 1/2 cup unsalted butter, melted
- 1 cup light brown sugar, packed
Instructions
- Preheat and prepare pan: Preheat your oven to 350°F (175°C). Grease a mini round cake pan or muffin tin thoroughly to prevent sticking.
- Cream butter and sugar: In a large mixing bowl, use an electric mixer to cream together the room temperature butter and granulated sugar until the mixture is light and fluffy, ensuring a smooth base for your cookie dough.
- Add eggs, vanilla, and sour cream: Incorporate the eggs, vanilla extract, and sour cream into the creamed butter and sugar mixture. Mix well until everything is fully combined and smooth.
- Mix dry ingredients: In a separate bowl, whisk together the all-purpose flour, baking powder, cornstarch, and salt to evenly distribute the leavening agents and seasoning.
- Combine wet and dry ingredients: Gradually add the dry ingredients to the wet mixture, stirring gently until just combined. Avoid overmixing to keep your cookies tender. Set the dough aside.
- Prepare the brown sugar glaze: In another bowl, mix the melted butter and packed light brown sugar together until smooth and well blended, creating a sticky, caramel-like topping.
- Add glaze to pan: Spoon about 1 tablespoon of the brown sugar mixture evenly into each cavity of the prepared pan, spreading it to cover the bottom.
- Add pineapple and cherry: Place one drained pineapple slice over each brown sugar layer. Then, position a maraschino cherry firmly in the center of each pineapple ring.
- Portion cookie dough: Using a 3-tablespoon scoop, evenly portion the cookie dough over each fruit-topped cavity, gently flattening the dough with an offset spatula to cover the fruit and glaze completely.
- Bake cookies: Bake in the preheated oven for 25 minutes or until the edges of the cookies turn golden and the brown sugar is bubbling around the sides, indicating caramelization.
- Cool and invert: Allow the cookies to cool in the pan for 10 minutes. Then carefully invert the pan onto a sheet of wax paper so the brown sugar glaze runs over the cookie tops, revealing the pineapple and cherries beautifully.
- Final cooling and storage: Let the cookies cool completely before serving. Store any leftovers in an airtight container to maintain freshness.
Notes
- Ensure butter is at room temperature for easiest creaming with sugar.
- Do not overmix the dough to keep cookies tender and soft.
- Use canned pineapple slices well-drained to avoid excess moisture in cookies.
- Invert cookies carefully as the brown sugar glaze will be hot and sticky.
- Store cookies in a cool, airtight container for up to 5 days, or freeze for longer storage.
