Pineapple Upside Down Cupcakes are the kind of dessert that instantly brightens up any table, bringing tropical charm and retro flair to even the simplest weeknight dinner. Imagine glossy, caramelized pineapple crowned with a cherry, nestled atop a buttery, ultra-moist cake with a hint of vanilla and pineapple juice. These individual treats put a playful twist on the classic cake, and thanks to their cupcake size, there’s no fighting over the best slice—everyone gets a perfect portion every time!

Pineapple Upside Down Cupcakes Recipe - Recipe Image

Ingredients You’ll Need

This recipe keeps things wonderfully straightforward, but don’t underestimate the impact of each ingredient—every one brings something special to the party, from tangy pops of fruit to that essential crumb and rich, buttery goodness.

Pineapple rings: Their sweet tang and juicy texture create the signature topping and infuse each cupcake with tropical flavor.
Maraschino cherries: Nestled in the center of each pineapple ring, these provide a pop of color and a hint of almondy sweetness.
Unsalted butter (melted): Brings richness to the topping and helps create that irresistible caramel base.
Brown sugar: This adds a warm, caramelly depth, marrying perfectly with the butter and fruit for a glossy, sticky finish.
All-purpose flour: Gives just the right structure for a tender cupcake crumb.
Granulated sugar: Balances the tart pineapple and amps up the sweetness in the cake itself.
Baking powder: Ensures the cupcakes rise high and stay fluffy.
Salt: Just a pinch sharpens and lifts all the other flavors.
Whole milk: Keeps the cake batter moist and adds richness.
Pineapple juice (reserved from the can): Doubles down on the pineapple flavor and ensures no wasted deliciousness.
Vanilla extract: Brings warmth and fragrance to the cake.
Large eggs: Add structure, richness, and moisture.
Vegetable oil: Locks in that ultra-moist texture we all crave in cupcakes.

How to Make Pineapple Upside Down Cupcakes

Step 1: Prepare the Topping

Start by mixing your melted butter with brown sugar until it’s combined and irresistibly gooey. Spoon about a tablespoon into the bottom of each muffin cup. This simple step is the secret to a perfect caramelized top (which will actually become the bottom—until you flip them!).

Step 2: Set Up the Pineapple and Cherries

Gently press a pineapple ring into each cup, right on top of your buttery brown sugar mix. Drop a maraschino cherry right in the center of every ring. This little burst of color is as pretty as it is tasty.

Step 3: Mix the Dry Ingredients

In a medium bowl, whisk together the flour, granulated sugar, baking powder, and salt. Giving these items a good whisk ensures your batter will bake up with a uniform and tender crumb.

Step 4: Blend the Wet Ingredients

In a separate bowl, whisk the milk, pineapple juice, vanilla extract, eggs, and vegetable oil until smooth and fully combined. The pineapple juice here is a flavor amplifier and adds the kind of tangy-sweet complexity that makes Pineapple Upside Down Cupcakes irresistible.

Step 5: Combine Batter and Assemble

Pour the wet ingredients into the dry mixture and stir just until you no longer see dry flour—overmixing can make cupcakes tough instead of tender! Divide the batter evenly among the muffin cups, filling each about two-thirds of the way, and make sure the batter covers the fruit toppings.

Step 6: Bake to Perfection

Set the muffin tin in your preheated oven and bake for 18 to 22 minutes, or until a toothpick inserted in the center comes out clean. The aroma of pineapple and caramel will let you know something magical is happening.

Step 7: Invert and Cool

Let the cupcakes cool in the pan for 5 minutes, then carefully invert the muffin tin onto a wire rack or tray. A little tap will set the cupcakes free, letting that luscious pineapple topping shine. Allow them to cool completely before serving—if you can wait that long!

How to Serve Pineapple Upside Down Cupcakes

Garnishes

A swirl of freshly whipped cream or a sprinkle of toasted coconut makes these cupcakes feel extra festive. Even a drizzle of reserved pineapple juice or a dusting of powdered sugar can elevate their already show-stopping look.

Side Dishes

Pair Pineapple Upside Down Cupcakes with light, tropical fruit salads or a scoop of creamy vanilla ice cream. For brunch, they play nicely alongside a platter of fresh berries and citrus segments.

Creative Ways to Present

Try arranging the cupcakes on a vintage cake stand for retro flair, or skewer a little wedge of pineapple and cherry for garnish. For parties, wrap each cupcake in parchment and tie with twine for a picnic-ready treat! These sunny desserts are always ready to steal the show.

Make Ahead and Storage

Storing Leftovers

Pineapple Upside Down Cupcakes are best enjoyed the day they’re made, but leftovers keep well! Place cooled cupcakes in an airtight container and store in the refrigerator for up to three days. The flavors will deepen, and the crumb stays remarkably moist thanks to the fruit topping.

Freezing

If you want to prepare in advance, these cupcakes freeze beautifully. Let them cool completely, then wrap each one in plastic wrap and place in an airtight, freezer-safe container. Freeze for up to two months—ideal for last-minute guests or tropical cravings in the winter!

Reheating

To reheat, simply bring cupcakes to room temperature, or gently warm them in the microwave for about 10-15 seconds. The topping will soften and the cake will taste deliciously fresh, as if just baked. Avoid over-heating to preserve the cake’s moist texture.

FAQs

Can I use fresh pineapple instead of canned?

Absolutely! Just be sure to cut the fresh pineapple into rings or tidbits that fit in your muffin tin, and use fresh or bottled pineapple juice in the batter if needed. Fresh pineapple brings a slightly tangier flavor and firmer texture.

What if I don’t have a muffin pan?

If you don’t own a muffin pan, a mini cake or ramekin can work in a pinch! Just be sure to watch the baking time closely, as the size and depth of your vessel may require adjustment.

Can I make these gluten-free?

Yes, substitute your favorite cup-for-cup gluten-free flour blend for the all-purpose flour. The pineapple keeps the cake beautifully moist, so you shouldn’t notice much difference in texture.

How do I keep the cupcakes from sticking?

It’s essential to grease your muffin tin thoroughly, especially around the rims. You can also run a small knife around each cupcake before inverting to help loosen any sticky spots from the caramelized topping.

How far in advance can I make Pineapple Upside Down Cupcakes?

You can make them up to 24 hours in advance. Store them covered in the refrigerator and let them come to room temperature before serving for the best flavor and texture.

Final Thoughts

With their sunny flavors and retro charm, Pineapple Upside Down Cupcakes are a dessert you’ll want to make again and again. They’re simple enough for a casual treat, yet impressive enough for company—a little bite of tropical joy, straight from your kitchen. Give them a try, and share the sweet magic with your favorite people!

Pineapple Upside Down Cupcakes Recipe

★★★★★

4.8 from 26 reviews

Author: Olivia
Total Time: 40 minutes
Yield: 12 cupcakes 1x
Diet: Vegetarian

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Description

Delight your taste buds with these individual Pineapple Upside Down Cupcakes. A classic dessert in a new form, these sweet treats are perfect for any occasion.

Instructions

Prepare Topping: Combine melted butter and brown sugar, spoon into muffin cups. Add pineapple ring and cherry to each.
Prepare Batter: Whisk flour, sugar, baking powder, and salt. In another bowl, combine milk, pineapple juice, vanilla, eggs, and oil.
Combine Ingredients: Mix wet ingredients into dry until just combined.
Fill Muffin Cups: Divide batter evenly, covering the pineapple and cherry topping.
Bake: Bake for 18-22 minutes at 350°F until a toothpick comes out clean.
Cool and Serve: Let cool in pan for 5 minutes, then invert onto a rack to cool completely before serving.

Notes

For added flavor, consider sprinkling a little cinnamon over the pineapple rings before adding the batter.
If you prefer a more caramelized topping, sprinkle a little additional brown sugar over the pineapple before adding the batter.

Prep Time: 20 minutes
Cook Time: 20 minutes
Category: Dessert
Method: Baking
Cuisine: American