Pineapple Upside-Down Cookies Recipe
These Pineapple Upside-Down Cookies combine the tropical sweetness of pineapple and the rich caramel flavor of brown sugar with a soft, buttery cookie base. Topped with maraschino cherries and a luscious caramelized glaze, these cookies bring a delightful twist to the classic upside-down cake in an easy-to-share bite-sized form, perfect for parties or everyday indulgence.
- Prep Time: 15 minutes
- Cook Time: 15 minutes
- Total Time: 30 minutes
- Yield: About 18 cookies 1x
- Category: Dessert
- Method: Baking
- Cuisine: American
Ingredients
Scale
Cookie Dough
- ½ cup unsalted butter, softened
- ¾ cup granulated sugar
- 1 large egg
- 1 tsp vanilla extract
- 1 ¼ cups all-purpose flour
- ½ tsp baking powder
- ¼ tsp salt
Topping
- ½ cup brown sugar
- 2 tbsp melted butter
- 1 small can pineapple rings, cut into smaller pieces
- Maraschino cherries, halved
Instructions
- Prepare the Cookie Dough: Preheat your oven to 350°F (175°C) and line a baking sheet with parchment paper or a silicone mat. In a mixing bowl, cream the softened butter and granulated sugar until light and fluffy using an electric mixer or whisk. Then add the egg and vanilla extract, mixing until smooth and glossy. In a separate bowl, whisk together the all-purpose flour, baking powder, and salt. Gradually add the dry ingredients to the wet mixture, stirring just until a soft dough forms, careful not to overmix.
- Prepare the Topping: In a small bowl, combine the melted butter and brown sugar until smooth to create the caramelized base for each cookie. Spoon about a teaspoon of this mixture onto the prepared baking sheet, spacing them apart to allow spreading.
- Assemble the Cookies: Place a small piece of pineapple on each brown sugar base, then top with a halved maraschino cherry. Scoop approximately 1 ½ tablespoons of the cookie dough, flatten slightly, and gently place it over the fruit and brown sugar mixture, pressing the edges lightly to seal the topping.
- Bake the Cookies: Bake in the preheated oven for 12-15 minutes until cookies are golden around the edges. Remove from the oven and allow them to cool on the baking sheet for 5 minutes to set the topping.
- Serve and Enjoy: Once completely cooled, carefully flip the cookies upside down to reveal the pineapple and cherry topping. Serve and enjoy these delightful pineapple upside-down cookies.
Notes
- If using salted butter, reduce the added salt in the dough accordingly.
- Brown sugar can be swapped for a deeper caramel flavor or omitted for a less sweet version.
- For an egg allergy substitute, use a flax egg: 1 tbsp ground flaxseed mixed with 3 tbsp water.
- Fresh pineapple can be used; cut into small tidbits for even baking.
- Maraschino cherries add color but dried cranberries or fresh cherries can be substituted.
- Do not overmix the dough to maintain a soft texture.
- Allow cookies to cool before flipping to ensure the caramel topping sets properly.
Keywords: pineapple upside-down cookies, tropical cookies, caramel cookies, fruity cookies, baking, dessert recipe
Find it online: https://bitesizedbenny.com/pineapple-upside-down-cookies-recipe/
