Mini Pineapple Upside-Down Cupcakes

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Mini Pineapple Upside-Down Cupcakes are the kind of dessert that make everyone smile before they even take a bite. With their golden caramelized pineapple topping and vibrant cherry center, these adorable little cakes are just as stunning to look at as they are delicious to eat. Whether you’re hosting a summer gathering, bringing treats to a party, or simply craving a bite-sized twist on a classic, these cupcakes deliver tropical flavor in every sweet, buttery mouthful.

Each mini cupcake is baked in a muffin tin, which gives you individual servings with perfectly crisp edges and soft, moist centers. The pineapple slices caramelize beautifully as they bake, while the brown sugar and butter melt into a luscious glaze. And the best part? They flip out of the pan looking like they came straight from a bakery.

Why You’ll Love This Mini Pineapple Upside-Down Cupcakes Recipe

This recipe brings the joy of a classic pineapple upside-down cake into mini, manageable portions that are perfect for parties or anytime you want a smaller treat. The ingredients are simple, the prep is quick, and the wow-factor is huge. Plus, you get that delicious buttery brown sugar topping in every bite without having to share a single slice.

These cupcakes are also great for making ahead. They store well and reheat beautifully, so you can enjoy them warm or cold, depending on your mood. They’re also a fun way to get kids involved in the kitchen with assembling the fruit and batter.

What Kind of Pineapple Should I Use?

For this recipe, canned pineapple rings work best because they are uniform in size and easy to cut down into the perfect shape for mini muffin tins. You’ll only need half a ring per cupcake, or even smaller wedges depending on your pan size. Make sure to use pineapple packed in juice, not syrup, so the flavor isn’t overly sweet. If you have fresh pineapple on hand, you can certainly use that as well—just make sure it’s sliced thin enough to soften during baking.

Ingredients for the Mini Pineapple Upside-Down Cupcakes

Making these Mini Pineapple Upside-Down Cupcakes doesn’t require anything fancy, but each ingredient plays an important role in making them sweet, moist, and visually stunning. You’ll find that you likely already have most of what you need on hand, and the tropical flavor twist adds a fun surprise to an everyday cupcake.

• Butter: Adds richness to the cupcakes and creates the irresistible caramelized topping when mixed with brown sugar.
• Brown Sugar: Helps create that deep, molasses-like glaze that pairs perfectly with the pineapple.
• Canned Pineapple Rings: Classic and convenient, they’re sliced and placed at the bottom of each cupcake mold.
• Maraschino Cherries: Add a pop of color and flavor right in the center of the pineapple.
• All-Purpose Flour: The foundation of the cupcake batter, providing structure.
• Granulated Sugar: Sweetens the batter without overpowering the fruit flavors.
• Baking Powder: Ensures your cupcakes rise perfectly in the oven.
• Salt: Just a pinch enhances all the sweet, buttery flavors.
• Eggs: Bind the batter together and add richness.
• Milk: Adds moisture to the batter for a tender crumb.
• Vanilla Extract: Brings warm flavor and depth to the cake.

How To Make the Mini Pineapple Upside-Down Cupcakes

Step 1: Prepare the Muffin Tin

Grease a 12-cup muffin tin generously with butter or nonstick spray. In each cup, place about half a teaspoon of melted butter followed by one teaspoon of brown sugar. Then add a small pineapple piece and one maraschino cherry in the center.

Step 2: Mix the Batter

In a medium bowl, whisk together the flour, baking powder, and salt. In a separate large bowl, cream the softened butter with the granulated sugar until light and fluffy. Beat in the eggs one at a time, then stir in the vanilla extract. Add the dry ingredients alternately with the milk until fully combined.

Step 3: Fill and Bake

Spoon the batter over the pineapple and cherry layer, filling each muffin cup about two-thirds full. Bake in a preheated oven at 350°F (175°C) for 20 to 25 minutes, or until the tops are golden and a toothpick inserted comes out clean.

Step 4: Cool and Invert

Let the cupcakes rest in the pan for about 5 minutes. Then run a knife around the edges and carefully invert them onto a wire rack or tray. Allow them to cool slightly before serving, so the caramelized topping sets just enough to hold.

How to Serve and Store These Mini Pineapple Upside-Down Cupcakes

These little tropical beauties are best served slightly warm when the caramelized brown sugar and pineapple topping is still gooey and luscious. You can enjoy them as-is, or with a scoop of vanilla ice cream or a dollop of whipped cream for an extra-indulgent treat. If you’re hosting a brunch or potluck, they also look charming when placed in cupcake liners for easy serving and cleanup.

This recipe yields 12 mini cupcakes, making it just right for small gatherings or sweet snacking throughout the week. To store them, place the cooled cupcakes in an airtight container and refrigerate for up to 4 days. You can reheat them for 10-15 seconds in the microwave to bring back that warm, just-baked texture. For longer storage, wrap them tightly and freeze for up to a month. Simply thaw at room temperature and warm briefly before serving.

What to Serve With Mini Pineapple Upside-Down Cupcakes?

Coffee or Cold Brew

The deep caramel notes in the cupcakes go perfectly with a bold cup of coffee or a splash of creamy cold brew.

Vanilla Bean Ice Cream

Add a scoop alongside your warm cupcake for a melty, dreamy combination of hot and cold.

Coconut Whipped Cream

A tropical twist on classic whipped cream that complements the pineapple and adds lightness.

Grilled Pineapple Slices

Double down on pineapple with some caramelized slices served on the side for a vibrant presentation.

Sparkling Water with Lime

For a light refreshment, pair your cupcakes with sparkling water and a squeeze of lime to brighten the palate.

Fresh Berries

Serve the cupcakes with a side of fresh strawberries or raspberries for a colorful plate and tart contrast.

Mango Sorbet

The bright, tangy flavor of mango sorbet is an unexpected yet delightful pairing.

Toasted Coconut Flakes

Sprinkle some on top of the cupcakes or your plate for added texture and island vibes.

Want More Tropical Dessert Ideas?

If you love these Mini Pineapple Upside-Down Cupcakes, you might just fall head over heels for these other fruity favorites too:

• Fried Pineapple with Coconut Crust is crispy, golden, and made for summer snacking.

• Air Fryer Pineapple offers that sweet roasted goodness with barely any effort.

• Tropical Teriyaki Chicken Kabobs with Pineapple are a fun dinner twist that brings dessert flavors to the grill.

• No-Bake Orange Creamsicle Pie brings the sunshine straight to your dessert table.

• Homemade Butter Pecan Ice Cream for when you want to pair your cupcakes with a creamy homemade scoop.

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And let me know in the comments how yours turned out. Did you go with canned or fresh pineapple? Add any special touches like rum extract or a sprinkle of cinnamon?

I love seeing your creative takes on these recipes and answering your baking questions too!

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