Pineapple Upside Down Cookies

Imagine biting into a soft, buttery cookie that captures all the tropical magic of a classic Pineapple Upside Down Cake in a convenient hand-held treat. These Pineapple Upside Down Cookies combine the caramelized sweetness of brown sugar, the tangy brightness of pineapple, and the nostalgia of maraschino cherries—all in perfect cookie form. The aroma of warm butter and caramelized pineapple will transport you straight to grandma’s kitchen, while the modern cookie format makes them perfect for today’s on-the-go lifestyle. You’ll learn how to create these delightful treats that blend retro charm with cookie convenience in just a few simple steps.

Why You’ll Love This Recipe

These Pineapple Upside Down Cookies offer everything you adore about the classic cake but with a delightful twist. The contrast between the soft, cake-like cookie base and the sticky-sweet caramelized pineapple topping creates a textural masterpiece that’s impossible to resist. Each bite delivers the perfect balance of buttery richness and tropical tanginess.

What makes these cookies truly special is their stunning presentation—the glistening pineapple ring topped with a bright cherry makes each cookie look like a miniature work of art, yet they’re surprisingly simple to prepare. Unlike the traditional cake that requires careful flipping and serving, these cookies are individual portions that travel well for potlucks, bake sales, or holiday cookie exchanges.

For busy bakers, these pineapple dessert cookies can be prepared in stages, with components made ahead of time. Plus, they’re versatile enough to be dressed up for special occasions or kept casual for everyday treats. Whether you’re a longtime fan of the classic dessert or trying this flavor combination for the first time, these cookies will quickly become a favorite in your baking repertoire.

Ingredients

For the Caramelized Pineapple Topping:

• 4 tablespoons (56g) unsalted butter
• 3/4 cup (150g) brown sugar, packed
• 1 can (20 oz/567g) pineapple rings, drained well (reserve 2 tablespoons juice for the cookie dough)
• 20-24 maraschino cherries, drained and patted dry

For the Cookie Dough:

• 2 1/2 cups (313g) all-purpose flour
• 1/2 teaspoon baking powder
• 1/4 teaspoon baking soda
• 1/2 teaspoon salt
• 3/4 cup (170g) unsalted butter, softened
• 1 cup (200g) granulated sugar
• 1/4 cup (50g) brown sugar, packed
• 2 large eggs, room temperature
• 1 teaspoon vanilla extract
• 2 tablespoons reserved pineapple juice
• 1/2 teaspoon almond extract (optional)

The canned pineapple rings are crucial for achieving that classic upside down pineapple cookie appearance, but fresh pineapple can be substituted if preferred. The combination of both granulated and brown sugar creates the perfect cookie texture while complementing the caramelized topping. Make sure your butter is truly softened for the dough—this ensures a tender, cake-like cookie that mirrors the texture of traditional pineapple upside down cake cookies.

Pro Tips

Master the Caramelization Process
The secret to perfect Pineapple Upside Down Cookies lies in properly caramelizing the topping. Cook the butter and brown sugar until it’s fully melted and just beginning to bubble—about 3-4 minutes—but don’t let it brown too much. This creates the signature sticky-sweet base that will gloriously coat your pineapple. Always pat your pineapple rings and cherries dry with paper towels before using; excess moisture will prevent proper caramelization and could make your cookies soggy.

Prevent Topping Transfer Issues
For flawless presentation, freeze your prepared topping circles for 15-20 minutes before adding them to the cookie dough. This solidifies the caramel mixture just enough to maintain the perfect circular shape and prevents the pineapple and cherry from sliding around when you transfer them onto the cookie dough. Use a thin spatula to move the frozen topping pieces for best results.

Perfect Your Cookie Base Texture
The ideal Pineapple Upside Down Cookie has a texture between a traditional cookie and cake. To achieve this, avoid overmixing your dough after adding the flour—mix just until combined. For an extra tender crumb, chill the assembled cookies for 20 minutes before baking. This prevents them from spreading too quickly in the oven and helps maintain that perfect cake-like texture that complements the caramelized fruit topping.

Instructions

Step 1: Prepare the Caramelized Pineapple Topping
Start by lining two baking sheets with parchment paper or silicone mats. In a medium saucepan over medium heat, melt the butter completely. Add the brown sugar and stir continuously until the mixture becomes smooth and bubbling, about 3-4 minutes. Remove from heat. Using a tablespoon, spoon 20-24 small circles of the caramel mixture onto the prepared baking sheets, spacing them at least 3 inches apart. Place one pineapple ring on each caramel circle, then add a maraschino cherry in the center of each ring. Place the baking sheets in the freezer while you prepare the cookie dough.

Step 2: Make the Cookie Dough
Preheat your oven to 350°F (175°C). In a medium bowl, whisk together the flour, baking powder, baking soda, and salt. In a large bowl or stand mixer, cream together the softened butter, granulated sugar, and brown sugar until light and fluffy, about 3 minutes. Add eggs one at a time, beating well after each addition. Mix in the vanilla extract, reserved pineapple juice, and almond extract if using. Gradually add the dry ingredients to the wet ingredients, mixing on low speed just until combined. The dough will be soft and somewhat sticky.

Step 3: Assemble and Bake the Cookies
Remove the prepared topping from the freezer. Using a cookie scoop or spoon, place about 2 tablespoons of dough on top of each pineapple ring. Gently press and shape the dough to cover the pineapple completely, being careful not to disturb the placement of the pineapple and cherry. Bake for 12-14 minutes, until the cookies are just set and the edges are lightly golden. The centers should still be soft. Allow the cookies to cool on the baking sheets for 10 minutes before carefully transferring them to a wire rack to cool completely.

Step 4: Finishing Touches
Once the cookies are completely cool, you may notice some caramel has pooled around the edges. This is perfectly normal and adds to their homemade charm! If desired, you can trim any excess caramel with kitchen scissors for a neater presentation. For an extra touch of sweetness and shine, brush the pineapple and cherry topping with a thin layer of warmed apricot jam or a simple glaze made from powdered sugar and pineapple juice.

Variations

Tropical Paradise Cookies
Transform your Pineapple Upside Down Cookies into an island getaway by adding 1/3 cup toasted coconut flakes to the cookie dough and substituting the almond extract with coconut extract. For an extra tropical punch, add 2 tablespoons finely chopped macadamia nuts to the dough. This variation pairs beautifully with a rum glaze made by mixing 1/2 cup powdered sugar with 1-2 tablespoons dark rum and drizzling it over the cooled cookies.

Mini Pineapple Cookie Cups
For bite-sized treats perfect for parties, convert this recipe into mini cookie cups. Use a mini muffin tin and place a small amount of the caramel mixture in each cup, topped with a small chunk of pineapple and a quarter of a maraschino cherry. Press small balls of cookie dough into each cup and bake for 8-10 minutes. These adorable mini pineapple upside down cookie cups make perfect one-bite desserts for gatherings and can be easily adapted for gluten-free guests by substituting a measure-for-measure gluten-free flour blend.

Storage and Serving

These Pineapple Upside Down Cookies are at their absolute best when enjoyed within the first two days after baking. Store them in an airtight container at room temperature, placing parchment paper between layers to prevent sticking. If you need to keep them longer, they’ll remain delicious for up to five days, though the caramelized topping may begin to soften the cookies slightly.

For make-ahead convenience, you can freeze the unbaked cookie dough discs (without the topping) for up to three months. When ready to bake, thaw overnight in the refrigerator, then prepare fresh caramelized pineapple topping before baking.

Serve these cookies slightly warm for the ultimate experience—15 seconds in the microwave brings back that fresh-baked magic. They pair beautifully with a scoop of vanilla ice cream for an elevated dessert, or alongside coffee for an afternoon treat. For a special brunch offering, arrange them on a platter with fresh pineapple chunks and mint sprigs for a visually stunning presentation that highlights these tropical treats.

FAQs

Can I use fresh pineapple instead of canned?
Yes, you can use fresh pineapple. Cut it into 1/4-inch thick rings and remove the core. However, fresh pineapple contains more moisture, so pat the rings very dry with paper towels and consider briefly cooking the fresh pineapple slices in the caramel mixture to release some moisture before assembling the cookies.

Why did my caramel topping harden too quickly?
If your caramel hardens before you can assemble the cookies, gently rewarm it over low heat until it becomes workable again. To prevent this issue, work with half the caramel batch at a time, keeping the remaining portion warm over very low heat.

Can I make these cookies ahead for a party?
Absolutely! Prepare the cookie dough up to 2 days ahead and refrigerate. You can also make and freeze the caramel pineapple topping pieces. On the day of your event, assemble and bake fresh cookies for the best presentation and flavor.

My cookies spread too much during baking. What went wrong?
Excessive spreading usually indicates the dough was too warm or the butter was too soft. Chill the assembled cookies for 20-30 minutes before baking, and make sure your baking sheets are cool before placing a new batch on them.

Can I make these without maraschino cherries?
Yes! The cherries are traditional but optional. You can substitute with fresh berries, a dollop of jam, or simply leave the center of the pineapple ring empty. The cookies will still capture the essence of a pineapple upside down cake with just the caramelized pineapple.

Conclusion

These Pineapple Upside Down Cookies are comfort food at its finest — a clever reinvention that captures all the nostalgic flavors of the classic cake in a convenient, hand-held format. The contrast between the caramelized fruit topping and the tender, cake-like cookie creates a perfect balance that’s impossible to resist. It’s the kind of treat that bridges generations, appealing to both those who cherish the traditional dessert and modern bakers looking for something uniquely impressive yet approachable. Whether shared at family gatherings, gifted to friends, or simply enjoyed with your afternoon coffee, these cookies bring a little tropical sunshine to any occasion.

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