Pineapple Upside Down Sugar Cookies are a delightful fusion of vintage charm and modern convenience. Inspired by the classic pineapple upside down cake, these cookies feature a soft, buttery sugar cookie base topped with sweet, juicy pineapple that caramelizes beautifully in the oven. They’re golden around the edges, tender in the center, and bursting with bright tropical flavor—perfect for anyone who loves nostalgic desserts with a fun, handheld twist.
Who Is This Recipe For?
This recipe is perfect for:
- Home bakers looking for an easy yet impressive dessert
- Pineapple lovers craving something beyond cake
- Busy cooks who want simple ingredients and quick prep
- Anyone baking for parties, holidays, bake sales, or family gatherings
- Beginners who want a foolproof cookie recipe
No special skills required—just mix, bake, and enjoy!
Why It’s Great
- Unique & eye-catching: Looks like a mini upside down cake
- Soft and buttery texture with a lightly caramelized topping
- Simple pantry ingredients you probably already have
- Faster and easier than making a full cake
- Perfect balance of sweet, fruity, and rich flavors
These cookies are proof that classic desserts can be reinvented in the best way.
Ingredients
- 1 cup unsalted butter, softened
- 1 cup granulated sugar
- 1 large egg
- 1 teaspoon vanilla extract
- 2 cups all-purpose flour
- 1 teaspoon baking soda
- ½ teaspoon salt
- 10–12 canned pineapple rings, well-drained and patted dry
- Extra granulated sugar, for sprinkling
Kitchen Equipment Needed
- Mixing bowls
- Electric mixer or hand whisk
- Measuring cups and spoons
- Baking sheets
- Parchment paper
- Cooling rack
Instructions
- Preheat oven to 350°F (180°C) and line baking sheets with parchment paper.
- Cream butter and sugar together until light and fluffy.
- Add the egg and vanilla extract, mixing until smooth.
- In a separate bowl, whisk flour, baking soda, and salt. Gradually mix into the wet ingredients until a soft dough forms.
- Scoop about 2 tablespoons of dough per cookie onto the baking sheet, spacing them 2 inches apart.
- Gently press a pineapple ring onto each cookie and sprinkle lightly with sugar.
- Bake for 11–13 minutes, until edges are lightly golden.
- Cool briefly on the tray, then transfer to a wire rack.
Storage
- Room temperature: Store in an airtight container for up to 3 days
- Refrigerator: Keeps well for up to 5 days
- Freezer: Freeze baked cookies (without pineapple browning) for up to 2 months
Tip: Place parchment paper between layers to prevent sticking.
FAQ
Can I use fresh pineapple instead of canned?
Yes, but make sure it’s very thinly sliced and well-dried to avoid excess moisture.
Can I make the dough ahead of time?
Absolutely! Refrigerate the dough for up to 24 hours before baking.
Why are my cookies spreading too much?
This can happen if the butter is too soft. Chilling the dough for 20–30 minutes helps.
Can I add cherries like the classic cake?
Yes! A small maraschino cherry piece in the center works beautifully.
Conclusion
Pineapple Upside Down Sugar Cookies are a fun, flavorful twist on a timeless dessert. With their soft texture, tropical sweetness, and nostalgic appeal, they’re guaranteed to stand out on any dessert table. Easy to make, beautiful to serve, and impossible to resist—these cookies prove that classic flavors never go out of style.
