Pineapple Upside Sugar Cookies: The Ultimate Cookie Recipe
Introduction to Pineapple Upside Sugar Cookies
Are you ready to embark on a delightful baking adventure? These Pineapple Upside Sugar Cookies are a wonderful blend of sweet pineapple, juicy cherries, and buttery cookie goodness! Perfect for family gatherings, potlucks, or just a treat for yourself, this recipe is sure to bring smiles to the faces of everyone who tries them. With their unique upside-down presentation and tropical flavors, these cookies are not just delicious but also a visual treat.
A Personal Story Behind My Pineapple Upside Sugar Cookies Journey
Growing up, my grandmother often made delightful desserts that filled our home with the warm aroma of baking. Pineapple upside-down cake was always a favorite, and I wanted to recreate that magic in a cookie form. This recipe brings back fond memories of family gatherings, laughter, and the joy of sharing delicious treats. Each time I bake these cookies, I feel that same warmth and love surrounding me.
What Makes This Pineapple Upside Sugar Cookies Recipe Special?
What sets this recipe apart is the delightful combination of flavors and textures. The soft, sweet cookie pairs perfectly with the juicy pineapple and cherries, creating a tropical experience with each bite. The use of brown sugar adds a rich depth that elevates these cookies beyond the ordinary. Plus, the upside-down style makes them visually appealing and fun to serve! Whether you’re an experienced baker or a beginner, these cookies are easy to make and sure to impress.
The Full Pineapple Upside Sugar Cookies Recipe
Ingredients
- 1 cup (226g) butter, room temperature
- 1 1/2 cups (300g) granulated sugar
- 2 eggs
- 2 tsp. vanilla extract
- 1/2 cup (120g) sour cream
- 3 cups (360g) all-purpose flour
- 1 tsp. baking powder
- 1 tsp. cornstarch
- 1/2 tsp. salt
- 13 canned pineapple slices
- 13 maraschino cherries
- 1/2 cup (113g) butter, melted
- 1 cup (200g) light brown sugar, packed
Instructions
- Preheat the oven to 350°F (175°C) and prepare a mini round cake pan. This ensures even baking.
- In a large mixing bowl, cream together the butter and granulated sugar until light and fluffy. This step is crucial for the texture of your cookies!
- Add the eggs, vanilla extract, and sour cream, mixing until well combined. The sour cream adds moisture and richness.
- Incorporate the flour, baking powder, cornstarch, and salt into the mixture, stirring until just combined to form the cookie dough. Avoid overmixing to keep your cookies tender.
- In a separate bowl, combine the melted butter and packed brown sugar until smooth. This will be the sweet base of your cookie cups.
- Spoon about a tablespoon of the brown sugar mixture into each cavity of the pan, spreading it evenly on the bottom. This creates a delicious caramel layer.
- Place a pineapple slice on top of the brown sugar with a maraschino cherry in the center. The cherry adds a pop of color and flavor!
- Scoop 3 tablespoons of cookie dough on top of the fruit. Flatten the dough with an offset spatula for even baking.
- Bake in the preheated oven for 25 minutes or until the edges are golden brown and the brown sugar is bubbling. Keep an eye on them to avoid overbaking.
- Allow the cookie cups to cool for 10 minutes, then carefully invert them onto a wax paper-covered surface to catch any drips. This is where the magic happens as they flip!
- Let the cookie cups cool completely before serving. Store in an airtight container and enjoy within 2-3 days for the best taste.
Serving Suggestions and Variations for Pineapple Upside Sugar Cookies
These delightful cookie cups can be served warm or at room temperature. They pair wonderfully with a scoop of vanilla ice cream or a dollop of whipped cream for an extra indulgent treat. For a fun twist, try adding a sprinkle of cinnamon or a dash of rum extract to the cookie dough for extra flavor. You can also experiment with different fruits like peaches or cherries for a new twist!
Frequently Asked Questions About Pineapple Upside Sugar Cookies
Can I use fresh pineapple instead of canned?
Yes, fresh pineapple can be used, but make sure it is ripe and cut into slices that are similar in size to canned slices.
How should I store leftover cookies?
Store the cookies in an airtight container at room temperature for up to 2-3 days. You can also freeze them for longer storage.
Can I make these cookies ahead of time?
Absolutely! You can prepare the cookie dough in advance and keep it in the fridge for a day or two before baking.
Is there an alternative to sour cream?
Yes, you can substitute Greek yogurt or buttermilk for a similar texture and flavor!

Pineapple Upside Sugar Cookies
Equipment
- Mini round cake pan For baking the cookie cups.
Ingredients
Main Ingredients
- 1 cup butter, room temperature
- 1.5 cups granulated sugar
- 2 tsp. vanilla extract
- 0.5 cup sour cream
- 3 cups all-purpose flour
- 1 tsp. baking powder
- 1 tsp. cornstarch
- 0.5 tsp. salt
- 13 canned pineapple slices
- 13 maraschino cherries
- 0.5 cup butter, melted
- 1 cup light brown sugar, packed
Instructions
- Preheat the oven to 350°F (175°C) and prepare a mini round cake pan.
- In a large mixing bowl, cream together the butter and granulated sugar until light and fluffy.
- Add the eggs, vanilla extract, and sour cream, mixing until well combined.
- Incorporate the flour, baking powder, cornstarch, and salt into the mixture, stirring until just combined to form the cookie dough.
- In a separate bowl, combine the melted butter and packed brown sugar until smooth.
- Spoon about a tablespoon of the brown sugar mixture into each cavity of the pan, spreading it evenly on the bottom.
- Place a pineapple slice on top of the brown sugar with a maraschino cherry in the center.
- Scoop 3 tablespoons of cookie dough on top of the fruit. Flatten the dough with an offset spatula.
- Bake in the preheated oven for 25 minutes or until the edges are golden brown and the brown sugar is bubbling.
- Allow the cookie cups to cool for 10 minutes, then carefully invert them onto a wax paper-covered surface to catch any drips.
- Let the cookie cups cool completely before serving. Store in an airtight container and enjoy within 2-3 days for the best taste.