Pineapple Upside-Down Cookies are a delightful twist on the classic Pineapple Upside-Down Cake. These charming cookies feature buttery vanilla dough topped with sweet caramelized pineapple and bright maraschino cherries, capturing all the nostalgic flavors of the beloved dessert in a perfectly portioned handheld treat.Each cookie offers a delicious contrast of textures and flavours.
Pineapple Upside-Down Cookies – Buttery Tropical Cookies
Ingredients
For the Topping
- ¼ cup unsalted butter, melted
- ½ cup packed brown sugar
- 1 cup finely chopped pineapple tidbits, well drained
- 12 Maraschino Cherry, halved
For the Cookie Dough
- ½ cup unsalted butter, softened
- ¾ cup granulated sugar
- 1 large egg
- 1 teaspoon vanilla extract
- 1¾ cups all-purpose flour
- 1 teaspoon baking powder
- ¼ teaspoon salt
- 2 tablespoons pineapple juice
Instructions
- Preheat the oven to 350°F (175°C). Line baking sheets with parchment paper.
- Mix melted butter and brown sugar. Place about 1 teaspoon of the mixture onto each cookie space. Top with a small spoonful of pineapple and half a cherry.
- Cream softened butter and sugar until light and fluffy. Beat in the egg and vanilla. Mix in pineapple juice. In a separate bowl, combine flour, baking powder, and salt, then add to the wet ingredients.
- Drop 1 tablespoon of dough over each pineapple topping, covering it completely.
- Bake for 12–14 minutes until the edges are lightly golden.
- Allow the cookies to cool for 3–4 minutes, then carefully flip them onto a cooling rack so the pineapple topping faces upward.
- Cool completely before serving.
Notes
- Drain the pineapple thoroughly to prevent soggy cookies.
- Pat cherries dry to reduce excess moisture.
- Use parchment paper for easier cleanup.
- Do not overmix the dough.
- Flip cookies while still warm.
- Finely chopped pineapple works best.
- Let cookies cool completely before storing.
- Store in an airtight container for up to 4 days.
Pineapple Upside-Down Cookies:
The soft, tender cookie base absorbs the rich brown sugar glaze, while juicy pineapple adds tropical sweetness and cherries provide a colorful finishing touch. They are eye-catching, festive, and wonderfully flavorful.Perfect for holiday trays, summer parties, bake sales, and afternoon tea, Pineapple Upside-Down Cookies are sure to impress. Their beautiful presentation and irresistible taste make them a memorable dessert that combines vintage charm with modern convenience.
History:
The original Pineapple Upside-Down Cake became immensely popular in the United States during the 1920s, following widespread availability of canned Pineapple. The cake’s signature caramelized topping and decorative cherries quickly made it a household favorite.As baking evolved, creative home cooks began adapting the iconic flavor combination into cupcakes, bars, and cookies. Pineapple Upside-Down Cookies emerged as a fun, bite-sized interpretation that preserves the dessert’s tropical character and striking appearance.
Subscribe to our youtube channel Kitchenpedia for more delicious recipes and hit the like button if you enjoyed this youtubevideo. Share it with your friends and Family.