Pineapple Upside Down Sugar Cookies Recipe
Sweet and tangy Pineapple Upside Down Sugar Cookies offer a fun twist on a classic dessert, featuring soft, buttery sugar cookies baked atop a luscious caramelized pineapple and cherry topping. These cookies deliver a delightful contrast of textures and flavors, making them perfect for parties, potlucks, or a special treat.
- Prep Time: 30 minutes
- Cook Time: 12 minutes
- Total Time: 60 minutes
- Yield: 16-20 cookies 1x
- Category: Dessert
- Method: Baking
- Cuisine: American
- Diet: Vegetarian
Ingredients
Scale
For the Cookie Dough:
- 2 ½ cups all-purpose flour
- 1 teaspoon baking powder
- ½ teaspoon baking soda
- ½ teaspoon salt
- 1 cup (2 sticks) unsalted butter, softened
- ¾ cup granulated sugar
- ¾ cup packed light brown sugar
- 2 large eggs
- 1 teaspoon vanilla extract
For the Pineapple Topping:
- ½ cup (1 stick) unsalted butter
- ¾ cup packed light brown sugar
- 1 (20 ounce) can pineapple slices, drained well and patted dry
- Maraschino cherries, halved (optional)
Instructions
- Prepare the Pineapple Topping: Melt ½ cup unsalted butter in a medium saucepan over medium heat until fully melted but not browned. Stir in ¾ cup packed light brown sugar and continue stirring constantly until sugar dissolves and mixture is smooth and glossy, about 2-3 minutes.
- Prepare the Baking Sheet: Line a large baking sheet with parchment paper. Pour the caramelized brown sugar mixture evenly onto the parchment and spread into a thin, even layer. Arrange drained pineapple slices on top of caramel layer, spacing about 2 inches apart. Place halved maraschino cherries in the center of each pineapple slice if desired.
- Make the Cookie Dough: In a medium bowl, whisk together flour, baking powder, baking soda, and salt. In a large bowl or a stand mixer bowl, cream softened butter, granulated sugar, and brown sugar until light and fluffy, about 3-5 minutes. Beat in eggs one at a time ensuring full incorporation, then add vanilla extract. Gradually add dry ingredients and mix on low speed just until combined, avoiding overmixing.
- Chill the Dough: Wrap the dough in plastic wrap and chill in the refrigerator for at least 30 minutes to prevent spreading during baking.
- Assemble Cookies: Preheat oven to 375°F (190°C) with the rack in the center position. Using a cookie scoop (about 1.5 tablespoons), portion dough and gently flatten each scoop into a disc. Place each dough disc on top of a pineapple slice on the prepared baking sheet and press gently to adhere.
- Bake: Bake the cookies for 10-12 minutes or until cookie edges are lightly golden brown. Watch carefully to avoid overbaking.
- Cool and Invert: Remove from oven and cool on the baking sheet for 5 minutes to allow caramel to set. Carefully invert the cookies onto a wire rack using a thin spatula to release any sticking cookies. Let cool completely before serving.
Notes
- Drain the pineapple thoroughly to prevent soggy cookies.
- Do not overbake to maintain soft, tender cookies.
- Use softened butter for better creaming and fluffy cookie texture.
- Chilling the dough is essential to minimize spreading during baking.
- Always use parchment paper for easy removal of sticky caramel topping.
- Try variations by adding cinnamon or nutmeg to dough or substituting different fruits for topping.
- Store cooled cookies in an airtight container at room temperature for up to 3 days.
Keywords: pineapple upside down cookies, sugar cookies, caramelized pineapple, dessert cookies, easy baking recipe, party cookies, tropical cookies
