Description
These Pineapple Upside-Down Sugar Cookies are a delightful twist on the classic pineapple upside-down cake. Featuring a soft and buttery sugar cookie base topped with caramelized brown sugar, melted butter, pineapple slices, and maraschino cherries, they offer a perfect balance of sweetness and tropical flavor. Baked to golden perfection, these cookies are ideal for parties, gatherings, or a special treat any time.
Ingredients
Scale
Cookie Dough
- 1 cup unsalted butter, softened
- 1 cup granulated sugar
- 1 large egg
- 1 teaspoon vanilla extract
- 2 ½ cups all-purpose flour
- 1 teaspoon baking powder
- ½ teaspoon baking soda
- ½ teaspoon salt
Topping
- 1 can (8 oz) pineapple slices, drained (reserve juice)
- ¼ cup unsalted butter
- ½ cup brown sugar, packed
- Maraschino cherries (one for each cookie)
Instructions
- Preheat Oven and Prepare Baking Sheets: Preheat your oven to 350°F (175°C) and line two baking sheets with parchment paper to prevent sticking and ensure even baking.
- Cream Butter and Sugar: In a mixing bowl, beat the softened butter and granulated sugar together for 3-4 minutes until light and fluffy, which creates a tender cookie texture.
- Add Egg and Vanilla: Incorporate the egg and vanilla extract into the creamed mixture, blending thoroughly to combine the flavors and moisture.
- Mix Dry Ingredients: In a separate bowl, whisk together the all-purpose flour, baking powder, baking soda, and salt to distribute the leavening agents evenly.
- Combine Dry and Wet Mixtures: Gradually add the dry ingredients to the butter mixture, stirring gently until the cookie dough just comes together. Avoid overmixing to keep cookies tender.
- Prepare Brown Sugar Topping: In a small saucepan over medium heat, melt ¼ cup unsalted butter with the packed brown sugar, stirring continuously until the mixture is bubbly and smooth to form a caramel-like sauce.
- Assemble Cookies on Baking Sheets: Spoon about one tablespoon of the brown sugar and butter mixture into the center of each cookie spot on the prepared baking sheets. Then place one pineapple slice on top of the brown sugar mixture for that classic upside-down look and flavor.
- Add Cherries: Place a maraschino cherry in the center of each pineapple slice, adding vibrant color and a sweet finishing touch.
- Top with Cookie Dough: Scoop about one tablespoon of cookie dough and gently spread it over each pineapple slice, covering the fruit slightly but keeping it visible for that signature pineapple upside-down presentation.
- Bake: Bake the cookies in the preheated oven for 12-15 minutes or until the edges turn a light golden brown, indicating they are cooked through.
- Cool: Let the cookies cool on the baking sheet for 5 minutes to set before transferring them to a wire rack to cool completely, which prevents them from breaking apart.
Notes
- You can substitute fresh pineapple slices for canned if preferred; just pat dry to remove excess moisture.
- For a softer cookie, do not overbake; remove from the oven when edges are lightly golden.
- Ensure butter is softened, not melted, before creaming with sugar to achieve the right texture.
- If you want a less sweet topping, reduce brown sugar to â…“ cup.
- Store cookies in an airtight container at room temperature for up to 4 days.
