Bright, buttery, and tropical. These soft rounds carry a sweet, caramelized aroma that fills the kitchen during a sunny Burbank afternoon. I love making these Pineapple Upside Down Cookies when I want the flavor of a classic cake without the heavy prep work. Olivia enjoys pressing the cherries into the center of each ring to finish them off. You need to bake these now for a cheerful treat that feels like a vacation in every bite.
Why This Recipe Stands Out
The primary benefit of this dish is its ability to deliver the nostalgic flavors of a traditional cake in a convenient, portable form. You also get the advantage of a short baking time and a beautiful presentation that brightens any dessert table. Ethan always reaches for these first because of the vibrant cherry center. These Pineapple Upside Down Cookies stand out because they use a simple shortcut to achieve a soft, consistent texture. Utilizing a Pineapple Upside Down Cake With Box Cake base ensures a reliable crumb that supports the juicy fruit topping perfectly.
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What You'll Use
Preparing these treats requires just a few pantry staples and some colorful fruit to create the signature look. You will find that these Pineapple Upside Down Cookies come together quickly thanks to the pre-mixed dry ingredients.
Scroll to the recipe card for ingredients and step-by-step directions.
Key Ingredients
- Yellow cake mix - provides a sweet, vanilla-scented foundation
- Butter - creates a rich and tender dough consistency
- Pineapple rings - adds a tropical, tangy sweetness to every bite
- Maraschino cherries - offers a bright pop of color and flavor
- Eggs - acts as the necessary binder for the cookie base
Optional Flavor Additions
You can add a sprinkle of shredded coconut to the dough for an extra layer of island-inspired texture. Incorporating a dash of rum extract creates a sophisticated Tropical Desserts profile that mimics a classic cocktail.
How to Make Pineapple Upside Down Cookies (Step-by-Step)
This method focuses on layering flavors for a result that is both soft and visually striking. Following these Mini Pineapple Upside Down Cakes steps ensures the fruit caramelizes beautifully without the dough becoming too soft.
Create Base
Combine the cake mix with melted butter and eggs to form a thick, uniform dough. This mixture should be firm enough to hold its shape while supporting the weight of the fruit.
Prepare Fruit
Drain the fruit slices thoroughly and pat them dry to remove excess syrup before assembly. Reducing surface moisture prevents the cookies from spreading too much or becoming soggy in the oven.
Should the fruit be fresh or canned? Canned fruit is preferred for this recipe because it is pre-softened and carries the consistent sweetness needed for a caramelized finish.
Assemble Rounds
Place the fruit rings onto the flattened dough mounds and press a cherry into each center. This ensures the toppings remain centered and secure during the expansion phase of baking.
Bake Set
Cook at 350°F until the edges are golden and the dough is fully baked through. High heat helps the sugars in the fruit caramelize against the buttery dough for a rich finish.
Aliana's Top Tip
I find that taking a few extra seconds to prep the fruit makes a huge difference in the final texture.
Cool on pan → lets the base set → ensures the cookie can support the fruit without breaking
Pat fruit dry → removes excess moisture → prevents the Pineapple Upside Down Cookies from becoming mushy
Use cold cherries → maintains their shape → results in a cleaner, more defined center
Space them out → allows for heat circulation → ensures the edges of the fruit caramelize evenly
Line your pans → prevents sticking → makes it easy to remove the sticky Pineapple Desserts Easy treats
Follow Aliana on Pinterest →Creative Modifications
For those who prefer smaller treats, you can use a muffin tin to create Bite Size Cookies with a more uniform shape. You can also swap the rings for a Crushed Pineapple Upside Down Cake style topping if you want fruit in every single bite. If you're looking for a homemade touch, try a Pineapple Upside Down Cake Recipe From Scratch dough base instead of the mix.
Storage Solutions
Store your cookies in a single layer in an airtight container to prevent the fruit from sticking together. These remain fresh in the refrigerator for up to three days, though the dough may soften slightly over time. To enjoy them later, a quick five-second warm-up in the microwave can restore the Pineapple Cookies to their original soft texture.
Serving Suggestions
I love serving these at room temperature for a bright addition to an Easter Dessert spread. They also work wonderfully as a light finish to a heavy meal when paired with a scoop of coconut sorbet. Adding a dusting of powdered sugar just before serving gives these Pineapple Bars a professional, finished look.
FAQs
Can I use fresh pineapple instead?
While fresh fruit can be used, it often contains more acid and varies in sweetness. Canned rings are more reliable for baking because they have a consistent sugar content that aids in the caramelization process required for this specific cookie style.
Why are my cookies spreading too much?
This usually happens if the butter was too hot when mixed or if the fruit wasn't dried properly. Ensure the dough is slightly chilled if your kitchen is warm, and always pat the fruit rings dry to keep the moisture levels balanced.
Do I need to use yellow cake mix?
Yellow cake mix is the traditional choice for its buttery flavor, but white or even spiced cake mix can be used for a different flavor profile. The Pineapple Upside Down Cake From Scratch method is also an option if you prefer to measure out your own flour and sugar.
Should I store these on the counter?
Because of the fresh fruit topping, these should be kept in the refrigerator if not eaten within a few hours. This keeps the pineapple fresh and prevents the buttery base from becoming too soft in warm environments.
Hungry for More
This recipe is a bright favorite in my Dessert collection.
Gave this recipe your own spin? Share it on Pinterest @AlianaRecipes - I can't wait to see your take on it!
Pineapple Upside Down Cookies
Ingredients
Equipment
Method
- Combine the cake mix, melted butter, and eggs in a large bowl until a thick, pliable dough forms. This mixture serves as the sturdy foundation for the fruit toppings.
- Scoop portions of dough onto a lined baking sheet and flatten them slightly to create a wide base for the fruit. The dough should be large enough to hold a full ring without overflowing.
- Press a fruit ring and a cherry firmly into the center of each dough mound to secure them before baking. This step ensures the toppings stay in place as the dough rises and expands. Should the fruit be fresh or canned? Canned fruit is preferred for this recipe because it is pre-softened and carries the consistent sweetness needed for a caramelized finish.
- Bake at 350°F for fifteen minutes until the edges are lightly toasted and the centers are set. You will notice the fruit appearing glossy and the dough becoming a pale golden color when finished.
Nutrition
Notes
Pairing
These are my favorite dishes to serve with Pineapple Upside Down Cookies:
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