Introduction
Few desserts carry the charm of a pineapple upside-down cake, but what if you could capture that tropical sweetness in a perfectly sized cookie? These Pineapple Upside Sugar Cookies are soft, buttery, and infused with caramelized pineapple flavor that instantly transports you to a warm, sunny day. With a chewy cookie base and a sweet pineapple topping, they make the perfect treat for gatherings, holiday platters, or even a simple weekday indulgence. In this post, I’ll walk you through everything you need to know to recreate this recipe in your own kitchen, from step-by-step instructions to variations and expert tips.
My recipe story
I first discovered the magic of pineapple upside-down treats during a family holiday party. My grandmother baked a gorgeous pineapple upside-down cake every year, and the combination of caramelized sugar with juicy pineapple slices was unforgettable. As I started experimenting in my own kitchen, I wanted to recreate that nostalgic flavor but with a fun twist—something more portable, bite-sized, and easy to serve at potlucks or picnics. That’s how these Pineapple Upside Sugar Cookies were born. Each cookie is like a mini version of the classic dessert, combining the buttery softness of sugar cookies with the tropical tang of pineapple. It’s a recipe that brings smiles and a bit of sunshine wherever it goes.
💡 Why You’ll Love This Recipe
- A unique twist on a classic pineapple upside-down cake, in convenient cookie form.
- Perfectly portioned for parties, bake sales, and gift boxes.
- Soft, chewy texture paired with juicy, caramelized pineapple topping.
- Easy-to-follow recipe that requires simple ingredients found in most kitchens.
- Customizable with variations like cherries, coconut, or spiced sugar toppings.
Ingredient breakdown
The beauty of this recipe lies in its simplicity. You’ll need pantry staples like butter, sugar, and flour, with pineapple taking the spotlight as the star ingredient. The butter provides richness and tenderness, while sugar sweetens and helps achieve the classic caramelization on top of the cookies. A single egg binds the dough together, and vanilla extract rounds out the flavor with a comforting aroma.
The pineapple adds natural juiciness and tang that balances the sweetness of the cookie base. You can use either fresh pineapple diced into small pieces or canned pineapple tidbits for convenience. Both work wonderfully, but canned pineapple tends to be more consistent in moisture and sweetness. The combination of these ingredients creates a harmonious balance between chewy cookie dough and juicy fruit topping that sets these cookies apart from traditional sugar cookies.
Flour and baking powder provide the structure, while a pinch of salt enhances all the flavors without overpowering the sweetness. Together, these ingredients create a soft yet sturdy cookie that can hold its topping without crumbling. When baked, the pineapple caramelizes slightly, creating a golden, glossy finish that’s just irresistible.
Equipment you’ll need
- Mixing bowls (medium and large)
- Electric hand mixer or stand mixer
- Measuring cups and spoons
- Baking sheet
- Parchment paper or silicone baking mat
- Cooling rack
- Spatula and spoon
- Sharp knife (if using fresh pineapple)
Step-by-step directions
Step 1: Prepare your baking sheet. Line a large baking sheet with parchment paper or a silicone baking mat. This will prevent the cookies from sticking and make cleanup a breeze. Preheat your oven to 350°F (175°C) so it’s ready once your dough is prepared.
Step 2: Cream the butter and sugar. In a large mixing bowl, beat 1 cup softened unsalted butter with 1 cup granulated sugar until light and fluffy. This should take about 2–3 minutes with an electric mixer on medium speed. Proper creaming ensures a tender cookie with a soft crumb.
Step 3: Add the wet ingredients. Beat in 1 egg and 1 teaspoon vanilla extract until fully incorporated. The mixture should look smooth and creamy. This step adds richness and enhances the overall flavor of the cookies.
Step 4: Mix the dry ingredients. In a separate bowl, whisk together 2 ½ cups all-purpose flour, 1 teaspoon baking powder, and ¼ teaspoon salt. Gradually add the dry mixture to the wet ingredients, mixing on low speed until a soft dough forms.
Step 5: Add the pineapple. Gently fold in 1 cup diced pineapple tidbits, making sure they are evenly distributed throughout the dough. Avoid overmixing, as this can cause the dough to become too wet.
Step 6: Shape the cookies. Scoop tablespoon-sized portions of dough and place them on the prepared baking sheet, spacing them about 2 inches apart. If desired, press a small extra piece of pineapple on top of each dough ball for added presentation and flavor.
Step 7: Bake. Place the cookies in the preheated oven and bake for 12–15 minutes, or until the edges are lightly golden and the tops are set. The pineapple will caramelize slightly, creating that signature glossy finish.
Step 8: Cool and serve. Allow the cookies to cool on the baking sheet for 5 minutes before transferring them to a cooling rack. This prevents breakage and helps the flavors set. Once cooled, enjoy them as they are or pair them with a beverage of your choice.
Variations & substitutions
Want to make this recipe your own? Try these creative twists:
- Add cherries: Place a maraschino cherry in the center of each cookie before baking for a classic upside-down cake look.
- Use coconut: Add ½ cup shredded coconut to the dough for a tropical flavor boost.
- Spiced version: Mix ½ teaspoon cinnamon or nutmeg into the dry ingredients for a warm, cozy variation.
- Gluten-free option: Swap all-purpose flour for a 1:1 gluten-free flour blend.
- Fresh vs. canned pineapple: Fresh pineapple offers a tart flavor, while canned gives a sweeter, more consistent result.
💡 Expert Tips & Troubleshooting
- Pat pineapple pieces dry before folding them into the dough to avoid excess moisture.
- If your cookies spread too much, chill the dough for 30 minutes before baking.
- For more caramelization, sprinkle a pinch of brown sugar on top of the cookies before baking.
- Don’t overbake—cookies should be slightly soft in the center when you remove them.
- Store cookies in layers with parchment paper between them to prevent sticking.
Storage, freezing & make-ahead
These cookies are best enjoyed fresh, but they also store well. Keep them in an airtight container at room temperature for up to 3 days. For longer storage, refrigerate them for up to 5 days. To freeze, place cooled cookies in a single layer on a baking sheet until firm, then transfer them to a freezer-safe bag. They’ll keep for up to 2 months. Thaw at room temperature before serving. You can also prepare the dough ahead of time, refrigerating it for up to 48 hours before baking. This makes it easy to bake a fresh batch whenever you need a quick dessert.
Serving ideas & pairings
Pineapple Upside Sugar Cookies shine on their own, but they also pair beautifully with other flavors. Serve them with a scoop of vanilla ice cream for a decadent dessert. Pair with coconut milk lattes or tropical fruit tea for a refreshing afternoon treat. For parties, arrange them on a platter with other fruit-inspired cookies or mini tarts for a colorful dessert spread. These cookies also make wonderful gifts—pack them in a decorative tin or clear bag tied with ribbon for a thoughtful homemade present.
FAQ
Can I use fresh pineapple instead of canned?
Yes, fresh pineapple works beautifully, but make sure to dice it small and pat it dry to prevent soggy cookies.
Do I need to refrigerate the dough before baking?
Not necessarily, but chilling the dough for 30 minutes helps control spreading if your kitchen is warm.
Can I make these cookies gluten-free?
Yes, simply replace the all-purpose flour with a gluten-free 1:1 baking blend.
How do I keep the cookies soft?
Store them in an airtight container with a slice of bread to maintain moisture and softness.
Can I double the recipe?
Absolutely. Just double all the ingredients and bake in batches as needed. These cookies are perfect for feeding a crowd.
Final thoughts
Pineapple Upside Sugar Cookies are a delightful twist on a nostalgic dessert, offering all the flavors of pineapple upside-down cake in a fun, bite-sized package. With their chewy cookie base, caramelized pineapple topping, and endless customization options, they’re bound to become a family favorite. Whether you’re baking for a holiday, gifting to friends, or simply treating yourself, these cookies bring sunshine to every bite. Give them a try, and you’ll see just how quickly they disappear from the plate!
Print
Pineapple Upside Sugar Cookies
- Total Time: 30 minutes
- Yield: 24 cookies
- Diet: Vegetarian
Description
 Soft, buttery cookies topped with caramelized pineapple for a tropical twist on a nostalgic classic. Perfect for parties and gifting.
Ingredients
- 1 cup unsalted butter, softened
- 1 cup granulated sugar
- 1 large egg
- 1 teaspoon vanilla extract
- 2 ½ cups all-purpose flour
- 1 teaspoon baking powder
- ¼ teaspoon salt
- 1 cup diced pineapple tidbits (fresh or canned, patted dry)
Instructions
- Preheat oven to 350°F (175°C) and line a baking sheet with parchment paper.
- In a large bowl, cream together butter and sugar until light and fluffy.
- Beat in the egg and vanilla extract until smooth.
- In a separate bowl, whisk together flour, baking powder, and salt.
- Gradually mix dry ingredients into the wet mixture until a soft dough forms.
- Fold in pineapple tidbits gently, avoiding excess liquid.
- Scoop tablespoon-sized dough balls onto the prepared baking sheet.
- Bake for 12–15 minutes, or until edges are lightly golden.
- Cool for 5 minutes on the pan, then transfer to a wire rack to cool completely.
Notes
Pat pineapple dry to prevent soggy cookies. Store in an airtight container for up to 3 days, or freeze for up to 2 months. Delicious served with vanilla ice cream or tea.
- Prep Time: 15 minutes
- Cook Time: 15 minutes
- Category: Dessert
- Method: Baking
- Cuisine: American