Pineapple Upside-Down Cupcakes Recipe

Get ready to fall in love with the playful twist of Pineapple Upside-Down Cupcakes! Imagine all the nostalgia and buttery sweetness of the classic cake, but downsized into adorable, single-serve treats. The caramelized pineapple and cherry topping bakes right into the top, infusing every bite with juicy flavor. These cupcakes are as gorgeous as they are delicious—they’re ridiculously easy and crowd-pleasing, perfect for parties, picnics, or whenever you want to brighten someone’s day (including yours!).

Ingredients You’ll Need

Ingredients You’ll Need

You won’t need anything fancy—just a handful of pantry staples and a few vibrant, fruity additions. Each ingredient in these Pineapple Upside-Down Cupcakes plays its part to deliver that iconic taste and irresistible presentation.

• Light brown sugar: Adds caramel-like richness to the upside-down topping and pairs beautifully with pineapple.
• Melted butter: Ensures the topping is buttery, gooey, and helps caramelize the sugar and fruit.
• Canned pineapple chunks: Save time and get perfect texture—just be sure to drain them well so your cupcakes aren’t soggy.
• Maraschino cherries: Bring a pop of color and a sweet, festive finish to each individual cupcake.
• Vanilla cupcake batter: Use your favorite boxed mix or a homemade recipe; this is the base that holds it all together!
• Vanilla extract: Rounds out the flavor, making every bite fragrant and bakery-level tasty.

How to Make Pineapple Upside-Down Cupcakes

Step 1: Prep Your Muffin Tin

Start by preheating your oven to 350°F (175°C) and greasing a standard muffin tin thoroughly. You can use nonstick spray, butter, or even muffin liners—just make sure every cup is well coated, so those beautiful tops release easily later.

Step 2: Create the Topping

Sprinkle about 1 teaspoon of brown sugar into the bottom of each muffin cup, then drizzle on a few drops of melted butter. This duo will form the rich, sticky caramel topping as your Pineapple Upside-Down Cupcakes bake.

Step 3: Add Pineapple and Cherries

Next, nestle a few pineapple chunks into each cup, arranging them for maximum coverage and cuteness. Pop a maraschino cherry right in the middle—this is what gives each cupcake its classic look with a bright, cheerful center.

Step 4: Mix the Batter

Prepare your vanilla cupcake batter according to the package or your favorite recipe, adding in the vanilla extract for an extra layer of flavor. Each cupcake only needs a little batter, so don’t overmix; just stir until everything is smooth and creamy.

Step 5: Assemble and Bake

Pour the cupcake batter gently over the fruit in each muffin cup, filling them about three-quarters full. Bake in the preheated oven for 18 to 22 minutes, or until the tops are golden and a toothpick comes out clean. Let them cool for about 5 minutes, then carefully invert each one onto a plate—prepare to wow yourself with the stunning, glossy fruit topping!

How to Serve Pineapple Upside-Down Cupcakes

Garnishes

While these cupcakes are striking on their own, you can sprinkle a little extra brown sugar on top or add a dusting of powdered sugar for sparkle. A dollop of whipped cream or a scoop of vanilla ice cream alongside each cupcake is pure bliss.

Side Dishes

Pair Pineapple Upside-Down Cupcakes with a fresh fruit salad, a tangy citrus sorbet, or a light yogurt parfait to keep the dessert feeling sunny and refreshing. If you’re serving at a brunch, they also complement savory quiches and breakfast sausage beautifully.

Creative Ways to Present

Try arranging the cupcakes on a tiered dessert tray for a show-stopping centerpiece. For parties, slip each into a colorful cupcake wrapper and add a little cocktail umbrella for extra tropical flair. You can even serve these cupcakes warm with a drizzle of caramel sauce for an indulgent finish.

Make Ahead and Storage

Storing Leftovers

Store any leftover Pineapple Upside-Down Cupcakes in an airtight container at room temperature for up to two days. If it’s particularly humid or you’re keeping them longer, stash them in the fridge—they’ll stay moist and delicious.

Freezing

These cupcakes are surprisingly freezer-friendly! Wrap each one tightly in plastic wrap (after they’re completely cool), then place them in a resealable bag. They’ll keep their flavor and texture for up to three months—perfect for spontaneous sweet cravings.

Reheating

To enjoy that just-baked experience, pop a cupcake in the microwave for about 10-15 seconds if it’s at room temperature, or up to 30 seconds from the fridge or freezer. The topping becomes soft and gooey again, as if you just pulled them from the oven.

FAQs

Can I use fresh pineapple instead of canned?

Absolutely! Fresh pineapple works great—just cut it into small chunks and pat them dry to avoid excess moisture in your cupcakes.

What if I don’t have maraschino cherries?

No worries—these Pineapple Upside-Down Cupcakes are still delicious without cherries, or you can substitute with another candied fruit or a fresh berry for a fun twist.

Can I make these Pineapple Upside-Down Cupcakes gluten-free?

Yes! Simply use your favorite gluten-free vanilla cupcake mix or recipe, and make sure all other ingredients fit your dietary needs.

Why did my cupcakes stick to the pan?

It’s important to grease the muffin tin very well, and let the cupcakes cool a few minutes before inverting. Running a thin knife around the edge can also help release them cleanly.

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

Drain the canned pineapple thoroughly and even pat the chunks dry with a paper towel. This ensures your Pineapple Upside-Down Cupcakes stay light and fluffy.

Final Thoughts

There’s something downright magical about flipping over these Pineapple Upside-Down Cupcakes and seeing their glossy, golden tops. Whether you bake them for a special gathering or just as a fun treat for yourself, I promise they’ll bring big smiles and an extra splash of sunshine to your table. Give them a try—you’ll be hooked on their charm (and taste!) in no time.

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