Save Soft, fluffy pineapple upside down sugar cookies instantly transport you to a tropical vibe no matter the season. Each cookie balances classic sugar dough with a buttery brown sugar base, juicy pineapple rings, and a bright maraschino cherry, making these delights perfect for celebrations or casual dessert cravings.
I tried these as a summer experiment and now they always vanish at potlucks and birthdays. There is something so charming about the sunny pineapple and sweet cherry nestled into a cookie.
Ingredients
- Butter at room temperature: makes dough smooth and adds rich flavor so pick unsalted high quality
- Granulated sugar: keeps the cookies sweet and fluffy choose superfine for best texture
- Large eggs: hold the dough together and boost moisture
- Vanilla extract: is key for warmth and aroma real vanilla makes a difference
- Sour cream: keeps cookies tender and slightly tangy whole fat gives best results
- All purpose flour: forms structure make sure to spoon and level to avoid dense dough
- Baking powder: gives a gentle rise check that yours is fresh
- Cornstarch: makes cookies soft and delicate look for a fine powder
- Salt: balances sweetness and rounds out flavors use fine sea salt if possible
- Canned pineapple slices: bring tropical juiciness choose slices in juice not syrup
- Maraschino cherries: add a huge pop of color and flavor seek out cherries with bright red color
- Melted butter: blends with brown sugar to form a gooey caramel layer choose European higher fat style for more flavor
- Light brown sugar: creates a buttery caramelized topping make sure it is soft and fresh
Instructions
- Prep the Oven and Pan:
- Preheat oven to 350 F or 175 C. Coat a mini round cake pan or muffin tin with nonstick spray or line with parchment for slick release.
- Cream the Butter and Sugar:
- In a large bowl, beat the butter with granulated sugar for at least three minutes until it turns pale and fluffy. This step promises cookies with soft middles.
- Add Eggs and Wet Ingredients:
- Mix in eggs one at a time then add vanilla and sour cream. Stir again just until blended. The dough should be creamy with no streaks.
- Combine Dry Ingredients:
- In another bowl whisk flour baking powder cornstarch and salt. Mixing fully here ensures even rising.
- Make the Dough:
- Gradually add dry mixture to the wet bowl stirring on low or by hand. Stop as soon as there are no dry bits left. Overmixing will toughen the cookies.
- Make the Brown Sugar Layer:
- In a small bowl stir melted butter and brown sugar until glossy and thick. This mixture becomes the caramel base.
- Assemble Pineapple and Cherries:
- Add one tablespoon of brown sugar mixture to each muffin cup. Spread to cover the bottoms completely. Lay a pineapple slice on top and nestle a maraschino cherry in its center.
- Top with Cookie Dough:
- Scoop three tablespoons of dough per cup. Use an offset spatula to lightly flatten the tops so the dough covers the fruit.
- Bake and Unmold:
- Bake for twenty five minutes until cookie edges look golden and the sauce is bubbling. Cool for ten minutes then carefully invert cookies onto wax paper. Use a spatula if fruit sticks to the pan. Let them cool before stacking or eating.
Save Light brown sugar is my favorite here because it never overwhelms the pineapple. I will never forget the first time I flipped the cookies over and saw the caramel bubbling with fruit — the kitchen filled with the happiest scent.
Storage Tips
Store extra cookies in a lidded container at room temperature for three days. Do not refrigerate as that dries the dough. Place wax paper between layers if stacking to keep fruit from sticking.
Ingredient Substitutions
Try Greek yogurt instead of sour cream for a similar effect. If you want to avoid dairy use plant based butter and coconut yogurt. Dark brown sugar will give a deeper molasses flavor but may overpower if you add too much.
Serving Suggestions
Serve with vanilla ice cream on warm days. For parties pile cookies high on a stand and top with extra cherries for a festive look. They also double as a sweet afternoon snack packed with coffee or tea.
Cultural and Historical Context
The original pineapple upside down cake grew popular in mid century America thanks to canned fruit and creative home bakers. Turning it into a cookie makes it picnic ready with all the same sunny nostalgia.
Seasonal Adaptations
Use fresh pineapple when in season but dry the slices well. In winter a pinch of cinnamon or cardamom in the brown sugar is flavorful. Try blood orange in place of pineapple for a different citrus blast.
Success Stories
Friends tell me these cookies wow guests at baby showers and brunches. One neighbor even made a double batch for a school bake sale and had nothing left but crumbs.
Freezer Meal Conversion
Flash freeze the assembled unbaked cookies in the pan. Once firm wrap well and freeze up to one month. Bake straight from frozen adding five extra minutes.
Save These cookies let you enjoy a sunny slice of cake wherever you are no forks or plates needed
Recipe FAQ
- → How can I prevent the pineapple from sticking to the pan?
Ensure the pan is well-coated with the brown sugar and butter mixture and invert the cookies soon after baking, while still warm.
- → Can I use fresh pineapple instead of canned?
Yes, fresh pineapple slices work great—just cut them to fit your pan and drain excess juice before adding.
- → Are these cookies suitable for a dairy-free diet?
Substitute dairy-free butter and sour cream to accommodate a dairy-free preference.
- → Can I make these cookies ahead of time?
Yes, these cookies stay fresh for 2–3 days when stored in an airtight container at room temperature.
- → What tools are recommended for best results?
A mini round cake pan or muffin tin ensures neat cookies, an electric mixer helps cream butter easily, and an offset spatula is perfect for smoothing the dough.