Mini Pineapple Upside-Down Cupcakes

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Sweet, golden, and irresistibly juicy—Mini Pineapple Upside-Down Cupcakes are the kind of treat that brings a tropical twist to any dessert table. These bite-sized beauties are everything you love about a classic pineapple upside-down cake, but in a charming, single-serve cupcake form. Perfect for parties, picnics, or a weekday dessert that feels like a mini vacation.

With caramelized pineapple rings and vibrant maraschino cherries sitting pretty on top, each cupcake hides a moist and buttery cake underneath. They’re the ultimate throwback dessert, dressed up for modern times—retro, fun, and incredibly photogenic. And the best part? They’re far easier to make than they look!

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Preparation Phase & Tools to Use

Before diving into this delicious recipe, gather your tools. Having the right equipment makes all the difference when you’re working with sticky toppings and delicate cupcake structures.

Essential Tools & Equipment:

• 12-cup Muffin Tin: The hero of this recipe. It allows the upside-down design to hold its shape while baking and ensures even cooking.
• Cupcake Liners (optional): While not required, they help with a cleaner release and make transporting the cupcakes easier.
• Mixing Bowls (Large & Medium): You’ll need these to mix the batter and prepare your topping mixture.
• Hand Mixer or Stand Mixer: For achieving that fluffy, well-creamed batter. A whisk could work in a pinch, but it’ll take more elbow grease.
• Measuring Cups and Spoons: Precision is key for baking success.
• Rubber Spatula: Great for scraping down the sides of bowls and for gently folding ingredients.
• Cooling Rack: Allows cupcakes to cool evenly and prevents soggy bottoms.

Using the correct tools helps streamline the process and guarantees each cupcake comes out with its iconic glossy pineapple-cherry crown intact.

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Ingredients for the Mini Pineapple Upside-Down Cupcakes

Each ingredient in this recipe plays a key role in both flavor and structure. Let’s take a look at what you’ll need:

• Canned Pineapple Slices: The star topping. Choose slices in juice (not syrup) for best flavor. Each ring gets halved to fit into muffin tins.
• Maraschino Cherries: Adds that sweet pop of color and classic flavor contrast.
• Brown Sugar: Creates the caramelized base that soaks into the cake. Light brown sugar is preferred for a balanced sweetness.
• Butter (unsalted): Used in both the topping and batter, it adds richness and tenderness.
• All-Purpose Flour: Provides structure. Make sure to measure it correctly for a fluffy crumb.
• Baking Powder: Ensures your cupcakes rise to the perfect height.
• Salt: A pinch balances sweetness and enhances flavor.
• Granulated Sugar: Adds sweetness to the batter without overpowering the pineapple.
• Eggs: Helps bind the batter and gives it structure.
• Milk: Adds moisture. Whole milk is best, but any milk works.
• Vanilla Extract: A touch of warmth and depth in the cake flavor.

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How To Make the Mini Pineapple Upside-Down Cupcakes

Step 1: Prep the Pan and Topping

Grease the muffin tin well. In each cup, add 1 teaspoon of melted butter followed by 1 teaspoon of brown sugar. Place half a pineapple ring and one cherry in the center. This becomes the beautiful top after baking.

Step 2: Mix the Batter Base

In a large bowl, cream together butter and granulated sugar until light and fluffy. Beat in the eggs, one at a time, then stir in vanilla extract.

Step 3: Combine the Dry Ingredients

In another bowl, whisk flour, baking powder, and salt. Gradually add this dry mixture to the wet ingredients, alternating with milk, and mix until just combined.

Step 4: Fill and Bake

Spoon the batter evenly over the pineapple-cherry base in the muffin cups, filling about 2/3 full. Bake in a preheated oven at 350°F (175°C) for 20–25 minutes until golden and a toothpick comes out clean.

Step 5: Cool and Flip

Let cupcakes cool for 5 minutes in the pan, then run a knife around the edges. Invert onto a tray or wire rack while still warm so the topping doesn’t stick.

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How to Serve and Store Mini Pineapple Upside-Down Cupcakes

These cupcakes are best served slightly warm or at room temperature, where the caramel topping stays glossy and the cake is at peak moistness. They pair beautifully with a scoop of vanilla ice cream or a dollop of whipped cream for a classic dessert experience.

To store, place leftovers in an airtight container and refrigerate for up to 3 days. For longer storage, freeze them individually wrapped in plastic and foil, then thaw at room temperature before serving. Reheat slightly to refresh the gooey top!

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Frequently Asked Questions

How do I keep the pineapple from sticking to the pan?

Be sure to grease the muffin tin generously and add the melted butter and brown sugar base before placing the fruit. This helps release the topping cleanly after baking.

Can I use fresh pineapple instead of canned?

Absolutely! Just make sure to cut it into thin rings or half-rings and remove any tough core. Fresh pineapple may be slightly less sweet.

Do I need cupcake liners?

They’re optional. You can skip them if you’re greasing the muffin tin well. Liners help with cleanup and make the cupcakes easier to handle.

What if I don’t have a hand mixer?

A whisk and strong arms can work in a pinch. Just make sure to cream the butter and sugar thoroughly for a fluffy texture.

Can I make these in advance?

Yes! Bake them the day before and keep covered at room temperature. If storing longer, refrigerate or freeze as noted above.

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Want More Cupcake Ideas with a Twist?

If you love these Mini Pineapple Upside-Down Cupcakes, you’ll probably enjoy these other creative takes on classic favorites:

• Grape Crush Cupcakes Recipe for a fruity and vibrant burst.
• Tiramisu Cupcakes Recipe if you’re craving coffee-flavored indulgence.
• Heavenly Raspberry Cheesecake Cupcakes for rich and creamy berry goodness.
• Almond Wedding Cake Cupcakes for a touch of elegance.
• Mini Cinnamon Roll Cheesecakes if you want a cozy and spicy dessert combo.

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Save This Recipe for Later

📌 Save this recipe to your Pinterest dessert board so you can come back to it any time: Life With Olivia on Pinterest

And let me know in the comments how yours turned out. Did you tweak the batter? Add a splash of rum? Try a different fruit topping?

I love hearing how others make these recipes their own. Questions are welcome too—let’s help each other bake smarter.

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