There’s just something magical about Pineapple Upside Down Cupcakes—they’re like a sweet little throwback to simpler times, but in the most adorable, bite-sized form. These cupcakes take the beloved classic pineapple upside down cake and shrink it into single-serving treats that are just as buttery, fruity, and caramelized as the original. You get juicy pineapple, a gooey brown sugar glaze, and that cheerful maraschino cherry right on top—each one a perfectly portioned dessert that looks as good as it tastes.

I first made these on a rainy Sunday afternoon when I was craving something nostalgic but didn’t want the fuss of a big cake. I was amazed at how easy they were to put together—no fancy tools, no complicated steps, just real ingredients and a little kitchen joy. If you’ve ever been intimidated by baking, don’t worry—these cupcakes are as beginner-friendly as it gets, and the results? Absolutely show-stopping.

Why You’ll Love This Recipe

Retro Charm Meets Cupcake Convenience

There’s something undeniably nostalgic about pineapple upside down cake—it’s the kind of dessert that brings back memories of vintage cookbooks and family gatherings. Now imagine all that goodness in a fun, single-serve cupcake. These Pineapple Upside Down Cupcakes take the charm of the 1950s classic and give it a delightful modern twist.
They’re perfect for sharing at potlucks, birthdays, baby showers, or even enjoying solo with a cozy cup of tea. No slicing needed—just grab one and enjoy a perfectly portioned bite of sunshine.

Simple, Everyday Ingredients

You won’t need to hunt down anything fancy to make these cupcakes. In fact, you probably have most of what you need in your pantry right now!
Canned pineapple, brown sugar, butter, and maraschino cherries are the stars of the show. Add a handful of baking basics like flour, sugar, and eggs, and you’re on your way. It’s the kind of recipe that feels accessible, even on a busy weekday, yet still tastes like you’ve made something truly special.

Foolproof Process

These cupcakes are practically made for beginner bakers—or anyone who wants great results without the stress. You won’t need a stand mixer or complicated techniques. Just a couple of bowls, a whisk, and a muffin tin.
The steps are simple and satisfying: melt butter, layer in the pineapple and cherry, mix the batter, and bake. It’s a great recipe to make with kids, too—they’ll love helping you place the cherries and sneaking a few along the way!

Easily Customizable

Want to make these cupcakes your own? Go for it!
Add a splash of rum or coconut extract for a more tropical flavor, or sprinkle in some toasted coconut or chopped nuts for added texture.
Need a gluten-free or dairy-free version? Easy. Just swap in your favorite 1:1 gluten-free flour blend and plant-based butter or oil.
It’s a recipe that adapts to your needs—because great baking should always feel personal.

Ingredients

Full List of Ingredients

Here’s everything you’ll need to bring these Pineapple Upside Down Cupcakes to life. Each ingredient plays a small but important role—just like every great recipe should.

12 maraschino cherries – These bright, candied gems sit right in the center, adding a sweet pop of color and flavor.
12 pineapple slices – Canned or fresh both work! They add tropical juiciness and that signature “upside down” look.
⅔ cup brown sugar – Melts beautifully into a sticky, caramel-like glaze underneath the pineapple.
½ cup melted butter – Rich, buttery goodness that forms the base of the topping.
1 ½ cups all-purpose flour – The sturdy structure that holds your cupcakes together.
1 cup granulated sugar – Sweetens the batter and gives a tender crumb.
⅓ cup vegetable oil – Adds moisture and softness to every bite.
1 ½ teaspoons baking powder & ¼ teaspoon baking soda – These two work together to give your cupcakes lift and fluff.
½ teaspoon salt – Just enough to balance all the sweet notes.
2 large eggs – Helps bind everything while adding richness.
½ cup pineapple juice – Adds flavor and moisture to the cake.
1 teaspoon vanilla extract – Rounds out the flavors with a warm, comforting aroma.

Simple, straightforward, and all easy to find—just the way we like it.

How to Make Pineapple Upside Down Cupcakes

Step-by-Step Instructions

Get ready to fill your kitchen with the scent of caramelized pineapple and buttery vanilla. These cupcakes are as fun to make as they are to eat—and they come together in just a few easy steps.

Preheat your oven to 350°F (175°C).
Give it time to heat up while you prep—this ensures even baking.
Lightly grease a 12-cup muffin tin.
You can use non-stick spray or a little butter. Don’t forget the sides!
Add about a teaspoon of melted butter into each muffin cup.
Then sprinkle about a tablespoon of brown sugar on top. This will form that glossy caramel-like topping.
Place a pineapple slice in each cup, and pop a maraschino cherry in the center.
It should look like a tiny edible flower!
In a large bowl, mix the dry ingredients: flour, sugar, baking powder, baking soda, and salt.
In a separate bowl, whisk together the wet ingredients: eggs, vegetable oil, pineapple juice, and vanilla extract.
Pour the wet ingredients into the dry and stir until just combined.
Be gentle here—overmixing can make your cupcakes tough.
Spoon the batter evenly over the pineapple slices, filling each cup about ¾ full.
This gives them room to rise without overflowing.
Bake for 20–25 minutes or until a toothpick inserted in the center comes out clean and the tops are golden.
Let the cupcakes cool in the pan for 5 minutes, then carefully invert them onto a wire rack or baking sheet.
They should pop right out, revealing that glossy, golden topping.

💡 Tip: Run a butter knife gently around the edge of each cupcake before inverting. It helps loosen any sticky bits for a perfect release.

What to Serve with Pineapple Upside Down Cupcakes

Suggested Pairings

These cupcakes are sunshine in dessert form, and they pair beautifully with a variety of treats and drinks. Whether you’re enjoying one solo or serving them at a get-together, here are some delicious ideas:

Drinks:
- Iced coffee
- Black tea
- Vanilla milkshake
Desserts:
- Coconut ice cream
- Lightly sweetened whipped cream
Other Pairings:
- Tropical fruit salad
- Grilled pineapple skewers

Variations and Substitutions

One of the best parts about Pineapple Upside Down Cupcakes is how easy they are to customize. Whether you’re baking for dietary needs or just want to switch things up, here are a few simple tweaks to try:

Make It Gluten-Free

Swap in a 1:1 gluten-free flour blend in place of the all-purpose flour. Look for one that includes xanthan gum for the best texture.

Make It Vegan

Replace the eggs with flax eggs (1 tablespoon flaxseed + 3 tablespoon water per egg) and use plant-based butter. The result is just as moist and flavorful—no compromise needed!

Add Texture

Sprinkle a little shredded coconut into the batter or on top before baking for a tropical twist. You can also toss in some chopped pecans for a nutty crunch that pairs beautifully with the pineapple.

Storage Instructions

Want to make your cupcakes ahead or save some for later? Here’s how to store them and keep that sweet, buttery topping just as tasty:

Room Temperature Storage

Store your cooled cupcakes in an airtight container for up to 2 days. Keep them in a cool, dry spot away from direct sunlight.

Refrigeration Tips

Need them to last a little longer? Pop them in the fridge for up to 5 days. Reheat gently in the microwave or a low oven to bring back that soft, warm texture.

Freezing Instructions

Wrap each cupcake tightly in plastic wrap, then place in a freezer-safe bag or container. They’ll stay fresh for up to 2 months.
To serve, thaw at room temp and warm in the oven at 300°F for about 5 minutes.

Recipe Tips and Tricks

These helpful little tips will take your cupcakes from good to truly bakery-worthy:

Use silicone muffin molds for a smoother release—no stuck-on topping!
Don’t skip the cherry—it adds color, sweetness, and nostalgia.
Try pineapple tidbits if you want a more rustic look or mini bites.
Let the cupcakes rest for 5–10 minutes before inverting—they’ll come out cleaner.
For a richer cake, swap a few tablespoons of oil with sour cream or Greek yogurt.

Related Recipes

If you loved these Pineapple Upside Down Cupcakes, you might also enjoy these other sweet and fruity treats:

Peach Bellini Cupcakes Light, fluffy cupcakes infused with peach and sparkling wine flavor.
Perfect Strawberry Cupcakes Recipe Sweet, moist cupcakes bursting with real strawberries.
Moscato Cupcakes Recipe Grown-up cupcakes made with Moscato wine—soft, floral, and fun.

FAQs

Here are some common questions readers ask about Pineapple Upside Down Cupcakes—you might be wondering the same thing!

Can I use fresh pineapple instead of canned?

Absolutely! Just slice it thinly and trim to fit your muffin tin. Add a touch of extra sugar if your pineapple isn’t super sweet.

Why did my cupcakes stick to the pan?

It’s likely the pan wasn’t greased well or the cupcakes cooled too long before flipping. Use nonstick spray and invert while still warm, after about 5 minutes.

Can I make these ahead of time?

Yes! You can bake them a day in advance. Just store in an airtight container and reheat briefly if desired.

What’s the best way to invert the cupcakes?

Place a wire rack or tray over the muffin tin, hold both firmly, and flip quickly and confidently. Most will slide right out with that glossy topping intact!

Conclusion

Pineapple Upside Down Cupcakes are a celebration in every bite—classic, charming, and oh-so-satisfying. Whether you’re baking them for a party, a weeknight treat, or a rainy afternoon pick-me-up, these cupcakes deliver on flavor, fun, and nostalgia.

They’re proof that baking doesn’t have to be complicated to be completely delightful. Even if you’re new to the kitchen, you’ve got this—and the results are totally worth it.