The sweet magic of pineapple upside-down cake is undeniable—juicy caramelized pineapple rings, a hint of brown sugar, and that tender cake texture. Now imagine transforming all that rich flavor into the convenience of a handheld treat. Enter: Pineapple Upside Sugar Cookies. These cookies bring together the buttery chew of a soft sugar cookie and the fruity caramel delight of classic upside-down desserts. Perfect for summer parties, holiday cookie trays, or whenever you’re craving something sweet and sunny, this cookie recipe is truly unforgettable.
These cookies are made with a rich sugar cookie base, topped with caramelized pineapple bits and maraschino cherries, delivering a taste of the tropics in every bite. If you’ve ever wanted to merge your love of cookies with your love for retro pineapple desserts, this is your dream come true.
Ingredients
For the Cookie Dough:
- 2 3/4 cups all-purpose flour
- 1/2 teaspoon baking powder
- 1/4 teaspoon baking soda
- 1/4 teaspoon salt
- 1 cup unsalted butter, softened
- 1 1/2 cups granulated sugar
- 1 large egg
- 1 teaspoon pure vanilla extract
- 1/2 teaspoon almond extract (optional, enhances the fruity flavor)
For the Pineapple Topping:
- 1 cup finely diced canned pineapple (drained and blotted dry)
- 1/4 cup light brown sugar, packed
- 1 tablespoon unsalted butter
- 1/2 teaspoon cinnamon (optional)
For Garnish:
- 12 maraschino cherries, halved
- Extra granulated sugar for rolling (optional)
Preparation
Step 1: Prepare the Pineapple Topping
In a small skillet, melt 1 tablespoon butter over medium heat. Add the diced pineapple and brown sugar, and stir continuously until the mixture starts to caramelize—about 6 to 8 minutes. Remove from heat and let cool completely. Optionally, stir in a pinch of cinnamon for extra warmth.
Step 2: Make the Sugar Cookie Dough
In a medium bowl, whisk together flour, baking powder, baking soda, and salt. Set aside.
In a large mixing bowl, cream the softened butter and granulated sugar using an electric mixer until light and fluffy—about 3–4 minutes. Add the egg, vanilla extract, and almond extract (if using), and beat until fully incorporated.
Gradually add the dry ingredients to the wet mixture and mix until a soft dough forms. If the dough is too sticky, refrigerate for 20–30 minutes for easier handling.
Step 3: Assemble the Cookies
Preheat your oven to 350°F (175°C). Line two baking sheets with parchment paper.
Scoop about 2 tablespoons of dough per cookie, roll into balls, and lightly press down to flatten. Using your thumb or the back of a spoon, create a shallow indentation in the center of each cookie.
Spoon a small amount of the cooled pineapple topping into the center of each cookie. Press a cherry half in the middle, cut-side down. Optional: Roll the dough balls in granulated sugar before pressing down for extra sparkle and crunch.
Step 4: Bake to Golden Perfection
Place cookies 2 inches apart on the baking sheet. Bake for 11–13 minutes, or until the edges are set and slightly golden but the centers are still soft. The cookies will continue to cook as they cool.
Remove from oven and allow to cool on the sheet for 5 minutes before transferring to a wire rack.
Step 5: Cool and Serve
Let the cookies cool completely before storing or stacking. The caramelized pineapple may be slightly sticky, so placing parchment between stacked cookies is recommended.
Variation
- Upside-Down Cookie Bars: Press dough into a square baking pan and layer pineapple topping evenly before baking. Slice into bars once cooled.
- Tropical Twist: Add shredded coconut to the dough or topping for even more island flavor.
- Gluten-Free Version: Use a 1:1 gluten-free baking flour blend to make this recipe accessible.
- Pineapple Coconut Sugar Cookies: Add 1/2 cup sweetened shredded coconut to the dough for added texture.
- Cream Cheese Frosting Drizzle: Drizzle with a tangy cream cheese glaze for a decadent finish.
COOKING Note
Make sure to drain and blot the pineapple very well before caramelizing. Extra liquid can cause your cookies to spread or become soggy. Allow your caramelized topping to cool fully before adding it to the cookie base to prevent melting the dough.
If making ahead, bake the cookies and store them separately from the topping to preserve their texture. Assemble before serving for the freshest results.
Serving Suggestions
Pineapple Upside Sugar Cookies pair beautifully with:
- A scoop of vanilla or coconut ice cream
- A refreshing summer cocktail like a piña colada or daiquiri
- A cup of black coffee or tropical tea
- A festive dessert board alongside chocolate chip cookies and coconut macaroons
Serve them warm for maximum gooey deliciousness, or chill slightly for a firmer bite.
Tips
- Chill the dough: Especially in warm kitchens, chilling prevents excess spread.
- Use parchment paper: Prevents sticking and makes clean-up easy.
- Perfect indent: Use the back of a tablespoon to get a uniform cavity for the topping.
- Don’t overbake: The cookies should be just set on the edges. They’ll firm up as they cool.
- Creative garnishes: Try a mint leaf on top for a fresh presentation twist.
Prep Time: 20 minutes
Cooking Time: 13 minutes
Total Time: 33 minutes
Nutritional Information
Calories: 210 | Protein: 2g | Sodium: 90mg | Saturated Fat: 6g | Unsaturated Fat: 4g | Trans Fat: 0g | Carbohydrates: 27g | Fiber: 0.5g | Cholesterol: 28mg
FAQs
Can I use fresh pineapple instead of canned?
Yes, but make sure it’s finely chopped and sautéed to remove excess moisture.
Can these cookies be made ahead?
Yes! Store baked cookies in an airtight container for up to 5 days. Add the pineapple topping just before serving for the best texture.
How do I store Pineapple Upside Sugar Cookies?
Keep them in a single layer or with parchment between layers in an airtight container. Store at room temperature or refrigerate for up to 5 days.
Can I freeze these cookies?
Yes. Freeze without the pineapple topping for up to 2 months. Thaw, warm slightly, and top before serving.
What makes the cookies chewy?
The butter-to-sugar ratio and baking time are key. Also, avoid overbaking for soft centers.
Conclusion
Pineapple Upside Sugar Cookies are a joyful fusion of old-school charm and modern cookie fun. With buttery sugar cookie dough, sweet caramelized pineapple, and a nostalgic cherry on top, each bite feels like a sunshine-filled treat. Whether for special occasions, gifting, or indulgent snacking, this recipe brings big smiles and bold flavors. It’s simple enough for beginners but unique enough to impress at any gathering.