Mini Pineapple Upside-Down Cookies Recipe

Get ready to wow your taste buds with Mini Pineapple Upside-Down Cookies, the bite-sized twist on a beloved retro dessert! These cookies are loaded with sunny pineapple flavor, caramelized brown sugar, and a cheery pop of maraschino cherry—all nestled on a buttery, tender cookie base. Every bite feels like a mini vacation, and they’re just as perfect for a festive party tray as they are for a cozy afternoon treat. If you’ve dreamed of the taste of classic pineapple upside-down cake, but wanted something cute, shareable, and easy to eat with your hands, this is the recipe you’ve been craving.

this Recipe

Ingredients You’ll Need

The magic of Mini Pineapple Upside-Down Cookies is how basic pantry staples transform into something truly special. Each element brings its own flair, whether it’s a dash of vanilla for warmth or a sprinkle of brown sugar for that caramelized finish.

• Unsalted butter (1/2 cup, softened): Gives the cookies a rich, melt-in-your-mouth texture and provides the perfect buttery base.
• Granulated sugar (3/4 cup): Sweetens the dough and also helps create the light, tender crumb.
• Large egg (1): Adds moisture and binds everything together for a cohesive, smooth dough.
• Vanilla extract (1 tsp): Enhances the overall flavor with its sweet, aromatic depth.
• All-purpose flour (1 1/2 cups): The structural backbone that gives the cookies their delightful bite.
• Baking powder (1/2 tsp): Ensures a little lift for the cookies, so they stay soft and fluffy.
• Salt (1/4 tsp): Balances the sweetness and brings out all the other flavors.
• Pineapple rings (6, cut into small circles): Each ring is cut to fit the cookies, adding tangy brightness and that signature tropical taste.
• Maraschino cherries (6, halved): For a pop of color and a hint of sweet-tart flavor right in the center.
• Brown sugar (2 tbsp): Caramelizes on top of the cookies, creating that classic upside-down cake magic.
• Butter for topping (2 tbsp): Melds with the brown sugar for a gooey, irresistible topping.

How to Make Mini Pineapple Upside-Down Cookies

Step 1: Prepare Your Baking Sheet

Preheat your oven to 350°F (175°C) and line a baking sheet with parchment paper. This simple prep step ensures your Mini Pineapple Upside-Down Cookies come off the tray easily and bake up evenly, preventing sticking and making cleanup a breeze.

Step 2: Cream the Butter and Sugar

In a large mixing bowl, beat together the softened butter and granulated sugar until light and fluffy. This step is key for creating a cookie that’s both tender and airy, as whipping air into the butter creates the perfect base for the dough.

Step 3: Add the Egg and Vanilla

Crack in the egg and pour in the vanilla extract, mixing until everything is beautifully combined. The egg binds the ingredients, while the vanilla introduces a layer of sweetness and aroma that ties every flavor together.

Step 4: Combine Dry Ingredients and Make the Dough

In a separate bowl, whisk together the all-purpose flour, baking powder, and salt. Gradually add the dry mixture to the wet ingredients, stirring just until a soft, smooth dough forms. Don’t overmix; you want to keep the cookies tender and light!

Step 5: Shape the Cookies

Scoop portions of dough (a tablespoon works well) and roll into small rounds, then gently flatten each one on your prepared baking sheet. The flattened shape provides the perfect canvas for your pineapple topping and ensures an even bake.

Step 6: Add the Pineapple Upside-Down Topping

Melt the brown sugar with 2 tablespoons of butter in a small saucepan over low heat until smooth and syrupy. Spoon a little of this mixture onto each cookie. Place a small pineapple piece on top, then nestle half a maraschino cherry right in the center. Each cookie should look like a mini version of the iconic upside-down cake!

Step 7: Bake and Cool

Slide the tray into your preheated oven and bake for 12 to 15 minutes, or until the edges turn golden and the tops are set. Let the cookies cool on the tray for a few minutes before transferring them to a wire rack. This lets the topping set and gives you neat, easy-to-eat cookies.

How to Serve Mini Pineapple Upside-Down Cookies

Garnishes

Makes these cookies extra special with a dusting of powdered sugar or a quick drizzle of vanilla glaze just before serving. The snowy effect of powdered sugar is simple but always impressive, while the glaze ups the sweetness factor for true dessert lovers.

Side Dishes

These bright, fruity cookies are perfect as part of an afternoon tea spread, paired alongside fresh fruit, or even grouped with other tropical treats like coconut macaroons or mango slices. The cookies also shine as a surprising finale to a summer barbecue with a scoop of vanilla ice cream on the side.

Creative Ways to Present

Bring out the big smiles by arranging your Mini Pineapple Upside-Down Cookies on a vintage cake stand or mini dessert plates. For parties, nestle each cookie into colorful cupcake liners. If you love entertaining, create a tropical-inspired dessert board with toasted coconut, extra cherries, and pretty flowers.

Make Ahead and Storage

Storing Leftovers

Keep your Mini Pineapple Upside-Down Cookies super fresh by storing them in an airtight container at room temperature for up to three days. Layer parchment or wax paper between each layer to prevent the gooey topping from sticking.

Freezing

Want to save some for later? These cookies freeze beautifully! Once cooled, arrange them in a single layer in a freezer-safe container. For longer storage, you can layer with parchment paper. They’ll stay at their best for up to two months—just thaw at room temperature before serving.

Reheating

If you like your Mini Pineapple Upside-Down Cookies slightly warm (highly recommended!), pop them in a 300°F (150°C) oven for a few minutes, or use a microwave at low power for about 10 seconds. The topping will become slightly gooey again, giving you that freshly-baked taste.

FAQs

Can I use canned pineapple for Mini Pineapple Upside-Down Cookies?

Absolutely! In fact, canned pineapple rings are perfect because they’re uniform and easy to cut into smaller rounds for each cookie. Just blot them dry before using to prevent soggy cookies.

How do I keep the topping from sliding off?

Let the cookies cool on the tray for at least 10 minutes before moving them to a wire rack. This helps the caramelized sugar set, keeping the pineapple and cherry neatly on top with every bite.

Can I make these cookies gluten-free?

Yes, swap the all-purpose flour for your favorite 1:1 gluten-free baking blend. The texture might change slightly, but you’ll still get the caramelized, pineapple-topped goodness in every bite.

Can I prep the dough ahead of time?

Definitely! The dough can be made and refrigerated (well-wrapped) for up to 2 days in advance. When you’re ready, just scoop, top, and bake—no need to bring to room temperature first.

What if I don’t have maraschino cherries?

If you’re out of maraschino cherries, try substituting with a fresh cherry, a blueberry, or even a dab of raspberry jam for a different fruity accent to your Mini Pineapple Upside-Down Cookies.

Final Thoughts

If you’re looking for a delightful, crowd-pleasing treat that delivers big on flavor and charm, don’t wait another minute—give these Mini Pineapple Upside-Down Cookies a try! They’re everything you love about the classic dessert in a handheld, happy little package, and sharing them is simply a joy.