Pineapple Upside Down Cake Cookies – Easy Tropical Dessert Recipe

Warm, buttery cookies topped with juicy pineapple and a cherry in the center—if that doesn’t make your mouth water, I’m not sure what will! The first time I made these pineapple upside down cake cookies, I actually surprised myself. I set out to combine my love for classic pineapple upside down cake with the fun, snackable joy of cookies. Let’s just say, now my kitchen smells like a tropical bakery every time I whip up a batch. It’s kind of magical how each bite takes you straight to a sunny island, with the sweet tang of pineapple and the cozy comfort of homemade cookies all in one.

I grew up eating pineapple upside down cake at family gatherings—my grandma used to make it for every holiday, and I swear, it was the first dessert to disappear. But cookies? Well, they’ve always been my go-to for sharing and gifting. So when I mixed the two, something clicked. Suddenly, these pineapple upside down cake cookies became the most requested treat in my house. There’s just something so cheerful about them—the pop of yellow, the glossy maraschino cherry, the caramel-like edges. They’re perfect for parties, bake sales, or just those days when you need a little sunshine on your plate.

Honestly, if you love bright, fruity flavors and soft, cake-like cookies, you’re in for a real treat. Plus, with this recipe, you don’t need any fancy ingredients or baking skills. Whether you’re baking with kids, prepping for a summer BBQ, or just treating yourself, these cookies tick all the boxes. Stick with me—I’ve tested this recipe more times than I can count, and I’ve got all the tips, tricks, and tropical twists to make your batch turn out irresistible every single time. Let’s get baking!

Why You’ll Love This Recipe

• Quick & Easy: You can have pineapple upside down cake cookies ready in under an hour. No cake pans or complicated steps—just scoop, top, and bake.
• Simple Ingredients: Pantry staples and a can of pineapple are all you really need! No hunting down obscure extracts or specialty flours.
• Perfect for Any Occasion: These cookies are a hit at summer parties, brunches, and even holiday cookie exchanges. They just look so bright and inviting on a platter.
• Crowd-Pleaser: There’s something about the combination of caramelized pineapple and a sweet cherry that gets everyone excited, both kids and adults.
• Unbelievably Delicious: The cookies have a soft, cake-like texture with buttery crisp edges—pair that with gooey fruit on top, and you’ve got a real flavor explosion.

I’ve tried dozens of pineapple upside down cake cookie recipes, but this one is truly special. Blending softened butter and brown sugar gives the base a rich, caramel note (just like the best upside down cakes). Adding a sprinkle of brown sugar under each pineapple ring helps the fruit caramelize in the oven, creating that iconic “upside down” flavor right on top of every cookie.

What really sets these cookies apart is their balance—sweet, but not cloying, with a hint of tang from the pineapple. And honestly, they’re as fun to look at as they are to eat! If you want a dessert that’s both nostalgic and a little bit whimsical, you’ve found it. These pineapple upside down cake cookies are the kind that people remember and ask for again and again. They’ll make you smile, I promise.

What Ingredients You Will Need

This recipe uses simple, wholesome ingredients to deliver bold, tropical flavor and a satisfying, soft texture—no complicated grocery lists here! Most of these are pantry staples, with a couple of special touches for that classic upside down cake vibe.

• For the Cookie Dough:
  • 1 cup (226g) unsalted butter, softened (adds richness; I like Kerrygold for extra flavor)
  • 1 cup (200g) packed brown sugar (for caramel notes)
  • 1/2 cup (100g) granulated sugar
  • 2 large eggs, room temperature
  • 2 teaspoons pure vanilla extract (or vanilla bean paste for extra depth)
  • 2 3/4 cups (345g) all-purpose flour
  • 1/2 teaspoon salt
  • 1 teaspoon baking powder
  • 1/2 teaspoon baking soda
• For the Topping:
  • 1 can (20 oz/565g) pineapple slices, drained well and patted dry (reserve juice for glaze, if you like)
  • Maraschino cherries, halved (about 12–16, depending on cookie size)
  • 1/4 cup (50g) packed brown sugar (for sprinkling under fruit)
• Optional Glaze:
  • 1 cup (120g) powdered sugar
  • 1–2 tablespoons reserved pineapple juice (or milk, for a thicker glaze)

Ingredient Tips & Substitutions:

• Butter: If you only have salted butter, reduce added salt to 1/4 teaspoon.
• Pineapple: Fresh pineapple works, just slice it thin and remove any tough core. Pineapple tidbits or crushed pineapple can be used for mini cookies.
• Flour: Swap with a 1:1 gluten-free flour blend if needed. Almond flour won’t work for this recipe.
• Cherries: No maraschino? Use candied cherries or even fresh, pitted cherries when in season.
• Eggs: For egg-free, use a flax egg (1 tablespoon flaxseed meal + 2.5 tablespoons water per egg), but note the dough will be slightly more tender.
• Brown Sugar: Light or dark both work, but dark brown sugar makes the topping extra caramelly.

Honestly, these ingredients are super flexible, so you can play around depending on what’s in your pantry or what’s in season. That’s part of the fun!

Equipment Needed

• Large Mixing Bowl: For creaming the butter and sugars. You can use a stand mixer or a regular hand mixer.
• Electric Mixer: Stand mixer with paddle attachment or handheld beaters—either works. A good spatula is handy for scraping the bowl.
• Baking Sheets: You’ll need two standard baking sheets. Line them with parchment paper for easy cleanup.
• Parchment Paper or Silicone Baking Mat: Prevents sticking and helps cookies bake evenly.
• Cookie Scoop (about 2 tablespoons): Makes portioning the dough so much easier. If you don’t have one, two spoons work just fine.
• Wire Rack: For cooling cookies quickly. If you don’t have one, just use a clean kitchen towel.
• Small Knife or Scissors: To halve the cherries and trim pineapple slices if needed.
• Measuring Cups and Spoons: Essential for accuracy—especially for baking!

If you don’t have an electric mixer, you can cream the butter and sugar by hand with a sturdy wooden spoon—just takes a bit more elbow grease. For the baking sheets, older pans may brown the bottoms faster, so keep an eye on your first batch. I always recommend lining with parchment; it keeps the caramelized fruit from sticking (trust me, I learned the hard way!). And if you’re baking on a budget, you can find great cookie scoops and wire racks at most dollar stores or thrift shops.

Preparation Method

1. Prep the Pineapple and Cherries (5 minutes):
   • Drain the pineapple slices very well and pat dry with paper towels. If they’re too wet, the cookies will spread too much.
   • Cut pineapple rings into quarters or halves, depending on cookie size. Halve the cherries.

   Tip: Extra moisture is your enemy—really press those slices dry!

2. Make the Cookie Dough (10 minutes):
   • In a large mixing bowl, cream together 1 cup (226g) softened butter, 1 cup (200g) brown sugar, and 1/2 cup (100g) granulated sugar until light and fluffy (about 2-3 minutes with a mixer).
   • Add in 2 eggs, one at a time, mixing well after each. Stir in 2 teaspoons vanilla extract.
   • In a separate bowl, whisk together 2 3/4 cups (345g) all-purpose flour, 1/2 teaspoon salt, 1 teaspoon baking powder, and 1/2 teaspoon baking soda.
   • Gradually add the dry mixture to the wet ingredients, mixing just until combined. Don’t overmix—the dough should be soft but not sticky.

   Warning: Overmixing makes the cookies tough, so stop as soon as you don’t see flour streaks.

3. Shape and Top the Cookies (10 minutes):
   • Using a cookie scoop or two spoons, portion out about 2 tablespoons of dough per cookie onto lined baking sheets, spacing at least 2 inches apart.
   • Gently flatten each ball with your palm or the bottom of a glass.
   • Sprinkle a pinch of brown sugar (from the 1/4 cup reserved for topping) on top of each cookie.
   • Press a piece of pineapple and a cherry half into the center of each cookie.

   Tip: If your pineapple pieces are big, press them in gently so they don’t slide off while baking.

4. Bake (12–15 minutes):
   • Bake at 350°F (175°C) for 12–15 minutes, until edges are golden and centers look just set.
   • Rotate pans halfway through for even browning.

   Sensory Cue: The cookies should smell buttery and you’ll see the pineapple caramelize slightly around the edges.

5. Cool (10 minutes):
   • Let cookies cool on the tray for 5 minutes (they’ll be soft!), then transfer to a wire rack to cool completely.

   Note: If you try to move them too soon, they might fall apart—so patience pays off here.

6. Optional Glaze (5 minutes):
   • Mix 1 cup (120g) powdered sugar with 1–2 tablespoons reserved pineapple juice until smooth.
   • Drizzle over cooled cookies for extra sweetness and shine.

   Tip: Let the glaze set for about 10 minutes before stacking or serving.

If your cookies spread too much, check that your butter wasn’t overly melted and your pineapple was well dried. If you want extra chewy cookies, chill the dough for 30 minutes before baking. And don’t stress if some cookies look a bit wonky—the homemade look is part of their charm!

Cooking Tips & Techniques

• Moisture Control: Pineapple upside down cake cookies get their signature look from the fruit topping, but too much liquid will sabotage your bake. Always dry pineapple slices thoroughly. Sometimes I even let them sit on paper towels for 10 minutes before using.
• Room Temperature Ingredients: Butter and eggs at room temp create a fluffier, more cohesive dough. Cold butter can make the cookies dense.
• Brown Sugar Sprinkle: Don’t skip the brown sugar under each fruit topping! It creates that caramel effect and keeps the pineapple from drying out in the oven.
• Spacing: These cookies spread a bit, so give them plenty of room on the tray. I once crowded a batch and ended up with a giant cookie “blob.” Tasted great—looked hilarious!
• Rotation: If your oven has hot spots (and let’s face it, most do), rotate your pans halfway through. This keeps the edges from overbaking and ensures even color.
• Chilling the Dough: For thicker, chewier cookies, chill the dough for at least 30 minutes. If you’re short on time, just pop the tray with shaped dough into the freezer for 10 minutes before baking.
• Doneness: Pull the cookies out when the edges are golden and the centers look just set. They’ll continue to firm up as they cool—if you wait until they’re firm in the oven, they’ll be dry.

One time, I forgot to dry the pineapple (oops), and my cookies spread into thin puddles with soggy middles. Lesson learned—prep the fruit! Multitasking helps: while the butter is creaming, get your toppings ready. And if you want picture-perfect cookies, use a cookie scoop for even sizing and prettier results. Consistency is key for that Pinterest-worthy batch!

Variations & Adaptations

• Gluten-Free Version: Swap the all-purpose flour for a 1:1 gluten-free baking blend. I’ve tried King Arthur and Bob’s Red Mill with great results. The cookies will be a touch more delicate but still delicious.
• Mini Cookies: Use pineapple tidbits or cut the rings into smaller pieces. Scoop tablespoon-sized dough balls for bite-size treats—perfect for parties or lunchboxes.
• Vegan Adaptation: Use vegan butter and flax eggs, and opt for plant-based milk in the glaze. Make sure your sugar is vegan-friendly (some brands process with bone char).

Flavor Twists: Add 1/2 teaspoon ground ginger or cinnamon to the dough for a cozy, spiced version. For extra zing, sprinkle a little lime zest over the finished cookies. And if you want a boozy grown-up twist, soak the pineapple in a splash of rum before topping!

Allergy Notes: If cherries are a concern, try dried cranberries or skip the topping. For nut lovers, a sprinkle of toasted coconut over the glaze is amazing.

My personal favorite? I sometimes add a handful of chopped macadamia nuts to the dough for crunch. Don’t be afraid to play around—these cookies are super forgiving!

Serving & Storage Suggestions

Serve pineapple upside down cake cookies at room temperature for the best texture—soft centers, just-crisp edges, and juicy fruit on top. They look gorgeous on a white platter, or line them up on a rustic wooden board for a tropical party vibe. Pair with iced coffee, sweet tea, or even a cold glass of pineapple juice for the full island effect.

For storing, let the cookies cool completely before placing them in an airtight container. They’ll keep on the counter for up to 3 days. If you want to keep them longer, store in the fridge for up to a week—they’ll stay soft, but bring to room temp before eating for best flavor. To freeze, layer cookies with parchment in a freezer-safe box; they’ll last up to 2 months. Thaw at room temperature (or sneak one frozen for a chewy, ice cream sandwich-like treat!).

To reheat, pop a cookie in the microwave for 10 seconds—just enough to revive that gooey pineapple topping. The flavors actually get deeper after a day, making them a great make-ahead dessert for gatherings. Honestly, they’re just as good on day three as they are fresh from the oven!

Nutritional Information & Benefits

Each pineapple upside down cake cookie is estimated to have about 160–180 calories, with 3g protein, 24g carbs, and 6g fat (based on standard ingredients and average size). Pineapple brings a boost of vitamin C and natural enzymes, while the cherries add a touch of antioxidants. The cookies are nut-free as written, and can be made gluten-free or dairy-free with simple swaps.

If you’re watching sugar, you can reduce the brown sugar in the dough by 1/4 cup and use no-sugar-added pineapple. These cookies are vegetarian and can be made vegan with easy substitutions. The main allergens are wheat, egg, and dairy—always check your ingredient labels if baking for sensitive eaters. For me, these cookies are a little indulgence that feels cheerful and bright, and I love that you can tweak them for almost any dietary need!

Conclusion

Pineapple upside down cake cookies are, hands down, one of those recipes that just never let me down. They’re tropical, a little nostalgic, and always manage to bring a smile—whether it’s for a summer cookout or a rainy day pick-me-up. I love how easy they are to customize and how they turn out picture-perfect every single time (even when life gets chaotic in the kitchen!).

If you’re looking for a dessert that tastes like sunshine and doesn’t require hours in the kitchen, you’ve got to try these. Don’t be afraid to toss in your own twists—maybe a sprinkle of coconut, a dash of spice, or even a chocolate drizzle. Let me know how yours turn out in the comments, and if you have a variation, I’d love to hear it! Happy baking, and may your cookies always be as sweet as a summer day.

Frequently Asked Questions

How do I keep the pineapple from making the cookies soggy?

Make sure to drain and pat the pineapple slices very dry before using. Excess moisture is the main reason for soggy cookies—sometimes I even let the slices sit on paper towels for a bit before baking.

Can I use fresh pineapple instead of canned?

Absolutely! Just slice it thin and remove the tough core. Fresh pineapple may have more juice, so dry it thoroughly to avoid spreading.

Can I make these cookies gluten-free?

Yes, use a quality 1:1 gluten-free flour blend in place of the all-purpose flour. The cookies will be a little more delicate but just as tasty.

Do I need to refrigerate pineapple upside down cake cookies?

They’re fine at room temperature for up to 3 days, but if your kitchen is warm or humid, store them in the fridge for up to a week. Bring to room temp before serving for the best texture.

What’s the best way to freeze these cookies?

Layer cooled cookies with parchment paper in a freezer container. Freeze for up to 2 months. Thaw at room temperature before serving—or enjoy them slightly chilled for a chewy treat!

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