Description
Pineapple Upside Sugar Cookies are a fun and irresistible twist on the classic pineapple upside-down cake. These cookies combine a soft, buttery sugar cookie base with a caramelized pineapple ring and a sweet maraschino cherry on top. Each bite delivers tropical flavor, nostalgic charm, and beautiful presentation in a perfectly portioned, handheld dessert.
Introduction
If you love pineapple upside-down cake but want something easier to serve and quicker to enjoy, these Pineapple Upside Sugar Cookies are the perfect solution. They capture everything that makes the classic dessert special, from the sticky caramelized fruit to the rich buttery base, while transforming it into a soft and chewy cookie.
These cookies are ideal for parties, bake sales, holidays, or anytime you want a dessert that looks impressive without being complicated. Baked in a muffin pan and flipped upside down, they reveal a glossy pineapple topping that makes them as eye-catching as they are delicious.
Why You’ll Love This Recipe
This recipe delivers the flavor of pineapple upside-down cake in cookie form
The cookies are soft, chewy, and rich with buttery flavor
They are individually portioned and easy to serve
The caramelized pineapple topping adds a tropical and nostalgic touch
Perfect for gatherings, celebrations, or special treats
Ingredients
For the Cookie Dough
1 cup unsalted butter, softened
1 cup granulated sugar
1 large egg
2 teaspoons vanilla extract
2½ cups all-purpose flour
1 teaspoon baking powder
¼ teaspoon salt
For the Pineapple Topping
½ cup brown sugar
¼ cup butter, melted
12 pineapple rings, drained and patted dry
12 maraschino cherries
Instructions
Prepare the Pan
Preheat the oven to 350°F (175°C).
Grease a muffin pan well or line with parchment rounds to ensure easy release.
Make the Caramel Base
In a small bowl, mix the brown sugar with the melted butter until combined.
Spoon about one heaping teaspoon of the mixture into the bottom of each muffin cup.
Add Pineapple and Cherry
Place one pineapple ring into each muffin cup on top of the caramel mixture.
Set a maraschino cherry in the center of each pineapple ring.
Prepare the Cookie Dough
In a large bowl, cream the softened butter and granulated sugar until light and fluffy.
Add the egg and vanilla extract and mix until smooth.
In a separate bowl, whisk together flour, baking powder, and salt.
Gradually add the dry ingredients to the wet mixture and mix until a soft dough forms.
Assemble the Cookies
Scoop about two tablespoons of dough and gently press it over each pineapple ring, fully covering the fruit.
Bake
Bake for 16 to 20 minutes, or until the cookie edges are lightly golden.
Cool and Flip
Let the cookies cool in the pan for 5 to 7 minutes.
Carefully run a knife around the edges and invert the pan onto a cooling rack to release the cookies.
Variations
Add a pinch of cinnamon or nutmeg to the cookie dough for warmth
Use crushed pineapple instead of rings for a rustic look
Swap maraschino cherries for candied cherries or fresh cherries
Drizzle with caramel sauce before serving for extra indulgence
Tips for the Best Results
Pat the pineapple rings completely dry to avoid excess moisture
Do not skip the caramel layer, as it creates the signature topping
Allow the cookies to cool slightly before flipping to prevent sticking
Use a muffin pan to keep the pineapple perfectly shaped
Storage Tips
Store cookies in an airtight container at room temperature for up to 2 days.
For longer storage, refrigerate for up to 5 days and bring to room temperature before serving.
Serving Suggestions
Serve with vanilla or coconut ice cream
Pair with iced tea, lemonade, or pineapple juice
Add a light dusting of powdered sugar for presentation
FAQs
Can I make these ahead of time
Yes, they can be baked a day in advance and stored in the refrigerator
Can I use canned pineapple
Yes, canned pineapple rings work perfectly, just be sure to drain them well
Can I freeze these cookies
Freezing is not recommended as the fruit topping may release moisture
Conclusion
Pineapple Upside Sugar Cookies bring together the best of two beloved desserts in one unforgettable treat. With their soft sugar cookie base, caramelized pineapple topping, and classic cherry center, they offer tropical flavor, beautiful presentation, and comforting nostalgia. Easy to make and impossible to resist, these cookies are sure to become a favorite in your dessert collection.