Description
These Pineapple Upside Sugar Cookies combine the tropical sweetness of pineapple and maraschino cherries with a soft, buttery sugar cookie dough. Each mini cake pan cavity is layered with a cinnamon-scented brown sugar glaze, pineapple slice, and cherry, then topped with cookie dough and baked to golden perfection. This nostalgic treat is perfect for any sweet tooth craving a fruity twist on traditional sugar cookies.
Ingredients
Scale
Cookie Dough
- 1 cup butter (room temperature)
- 1 ½ cups granulated sugar
- 2 eggs
- 2 teaspoons vanilla extract
- ½ cup sour cream
- 3 cups all-purpose flour
- 1 teaspoon baking powder
- 1 teaspoon cornstarch
- ½ teaspoon salt
Topping
- 13 canned pineapple slices
- 13 maraschino cherries
- ½ cup melted butter
- 1 cup packed light brown sugar
Instructions
- Preheat oven and prepare pan: Preheat your oven to 350°F (175°C). Lightly grease a mini round cake pan to prevent sticking and ensure easy removal of cookies after baking.
- Cream butter and sugar: In a large bowl, use a mixer to cream the softened butter with granulated sugar until the mixture becomes light and fluffy, which helps create a tender cookie texture.
- Add wet ingredients: Beat in the eggs, vanilla extract, and sour cream until everything is fully combined, making the dough smooth and moist.
- Incorporate dry ingredients: Gradually blend in the all-purpose flour, baking powder, cornstarch, and salt until a soft dough forms, ensuring no lumps remain.
- Prepare brown sugar topping: In a separate small bowl, combine the melted butter and packed light brown sugar; mix until smooth to create a caramel-like glaze.
- Assemble cookies: Spread about 1 tablespoon of the brown sugar mixture into each cavity of the mini cake pan. Place a pineapple slice on top of the brown sugar, then position a maraschino cherry in the center of each pineapple slice.
- Add cookie dough: Spoon approximately 3 tablespoons of the prepared cookie dough over each pineapple slice, gently pressing it down to fully cover the fruit and topping.
- Bake: Place the pan in the preheated oven and bake for about 25 minutes, or until the cookie dough is golden brown and cooked through.
- Cool and remove: Allow the cookies to cool in the pan for 10 minutes to set the shape, then carefully turn them out onto wax paper or a wire rack to cool completely before serving.
Notes
- Mini round cake pans are essential to achieve the classic pineapple upside-down cookie shape.
- Ensure butter is at room temperature for easy creaming with sugar.
- Cooling the cookies in the pan helps them hold their shape before being removed.
- Use canned pineapple slices with juice drained to avoid excess moisture in the cookies.
- These cookies can be stored in an airtight container at room temperature for up to 3 days.
