Description
These Pineapple Upside Down Sugar Cookies are a delightful twist on the classic pineapple upside down cake. Featuring a soft, buttery sugar cookie base topped with caramelized brown sugar, juicy pineapple slices, and maraschino cherries, they combine rich flavors with a fun presentation. Perfect for parties, afternoon treats, or anytime you crave a tropical-inspired dessert.
Ingredients
Scale
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: Preheat your oven to 350°F (175°C). Grease a mini round cake pan or a 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 unsalted butter and granulated sugar until the mixture is light and fluffy, creating a smooth base for the cookies.
- Add Wet Ingredients: Mix in the eggs, vanilla extract, and sour cream to the creamed butter and sugar, ensuring all ingredients are fully combined for a moist cookie dough.
- Combine 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.
- Mix Dry into Wet: Gradually incorporate the dry ingredients into the wet mixture, stirring gently until just combined to prevent overmixing and tough cookies. Set the dough aside.
- Prepare Brown Sugar Glaze: In another bowl, blend the melted unsalted butter with the packed light brown sugar until smooth and uniform to create the caramel-like glaze.
- Assemble Base Layer: Spoon approximately one tablespoon of the brown sugar mixture into each cavity of the prepared pan, spreading it out evenly to form a base layer for the fruit.
- Add Fruit Toppings: Place a drained pineapple slice on top of the brown sugar layer in each cavity. Position a maraschino cherry in the center of each pineapple ring for color and flavor.
- Add Cookie Dough: Using a 3-tablespoon scoop, portion the cookie dough over each fruit-topped cavity. Gently flatten the dough with an offset spatula to ensure even baking and coverage.
- Bake: Bake the cookies for 25 minutes, or until the edges turn golden brown and the brown sugar glaze starts bubbling up the sides, signaling readiness.
- Cool and Invert: Allow the cookies to cool in the pan for 10 minutes. Carefully invert the cookies onto wax paper so the brown sugar glaze runs over the tops, creating the signature upside-down effect.
- Final Cooling and Storage: Let the cookies cool completely before serving. Store any leftovers in an airtight container to preserve freshness and flavor.
Notes
- Make sure the pineapple slices are well drained to prevent soggy cookies.
- Use an offset spatula to evenly flatten cookie dough for consistent baking.
- Storing cookies in an airtight container helps maintain their softness.
- You can use a mini muffin pan if a mini round cake pan is unavailable.
- For variation, consider adding a sprinkle of toasted coconut on top after baking.
