Pineapple Upside Down Cupcakes

There’s something timeless about the charm of a pineapple upside-down cake. But what if you could capture that same nostalgic sweetness in the palm of your hand? That’s where these Pineapple Upside Down Cupcakes come in.

I made these cupcakes on a whim for a casual weekend get-together. I wanted a dessert that felt classic but was easy to serve without slicing or plating. Everyone loves the gooey caramelized pineapple topping, but presenting it in cupcake form just made it more delightful—and way more convenient. No forks, no mess, just a small bite of happiness.

This recipe is the perfect mashup of comfort and creativity. It’s not just another cupcake—it’s a portable, perfectly portioned piece of tradition. And once you see how easy they are to make (with pantry-friendly ingredients), you’ll find yourself making these again and again.

So if you’re looking for a dessert that’s just as pretty as it is delicious, and you love recipes that bring people together, keep reading. These cupcakes might just become your new go-to sweet treat.

Why I Love This Recipe

One bite into these cupcakes and you’re transported straight into dessert heaven—where brown sugar caramel, buttery cake, and tangy pineapple all live in perfect harmony.

What makes these cupcakes truly special is the transformation that happens during baking. You start with simple ingredients layered upside down—pineapple, brown sugar, a cherry—and then the magic happens in the oven. The sugar melts, the fruit caramelizes, and the cake rises to seal in all that sweet, sticky goodness.

But here’s what sets these apart: they’re individually portioned. You don’t have to commit to a whole cake, and there’s something festive about flipping over a tiny cupcake to reveal the glossy fruit top. It makes for such a satisfying presentation.

Plus, they’re crowd-pleasers. Adults love the retro vibes, and kids are drawn to the pop of color and sweet fruity flavor. Whether you’re baking for a party, a holiday, or just because you have a can of pineapple in the pantry, these cupcakes deliver every single time.

They’re also a perfect balance of moist cake and caramelized topping—without being overly sweet. That balance is why I come back to this recipe often, and why I think you’ll fall in love with it too.

Ingredients for Pineapple Upside Down Cupcakes

Let’s talk ingredients—and why each one matters.

This recipe doesn’t require anything fancy, and you probably already have most of what you need in your pantry and fridge. The magic comes from how these ingredients work together in layers to create that signature upside-down effect.

Here’s what you’ll need and why:

For the topping (the “upside-down” part):

• Canned pineapple slices – Make sure they’re in juice, not syrup. You’ll use the slices and a bit of juice. Cut them to fit in your cupcake tin.
• Maraschino cherries – These aren’t just for color—they add a subtle fruity sweetness that pairs beautifully with the pineapple.
• Unsalted butter – Melted butter mixes with the sugar to form that golden, sticky glaze.
• Light brown sugar – This is key for creating that gooey, caramelized topping. Don’t use white sugar here—it won’t melt the same way.

For the cupcake batter:

• All-purpose flour – Your structure. Sift it if you can—it keeps the texture light.
• Baking powder – Helps the cupcakes rise and stay fluffy.
• Salt – Just a pinch enhances all the other flavors.
• Unsalted butter (softened) – For richness and moisture. Let it sit out ahead of time.
• Granulated sugar – Sweetens the cake without overwhelming the pineapple.
• Large eggs – Help bind the batter and give it structure.
• Whole milk – Adds moisture and softness to the crumb.
• Vanilla extract – Adds depth and warmth to the flavor.
• Reserved pineapple juice – Just a splash gives a hint of fruity flavor in the cake itself.

These ingredients work in harmony to give you soft, buttery cupcakes topped with a golden pineapple crown.

How Much Time Will You Need

These cupcakes are pretty quick to make, considering how impressive they look when done. Here’s a time breakdown:

• Prep time: 20 minutes
• Bake time: 22 to 25 minutes
• Cool and flip time: 10 to 15 minutes

In total, you’re looking at about 50 to 60 minutes from start to finish, including cooling time. Not bad for a dessert that looks like it came from a bakery window.

How to Make These Pineapple Upside Down Cupcakes

This is where the magic happens. Follow these steps closely, and you’ll be rewarded with cupcakes that look as amazing as they taste.

Step 1: Prepare the cupcake pan

Preheat your oven to 350°F (175°C). Lightly grease a 12-cup muffin pan with non-stick spray or butter. You can use liners, but I recommend skipping them so the topping can flip out cleanly.

Step 2: Create the topping

In a small bowl, mix ¼ cup of melted unsalted butter with ⅔ cup of packed light brown sugar. Spoon about 1½ teaspoons of this mixture into the bottom of each muffin cup.

Cut each pineapple slice into quarters or halves, depending on the size of your muffin tin. Place one or two pieces in each cup over the brown sugar mixture.

Add a maraschino cherry in the center of each cup, gently pressing it down into the sugar mixture.

Step 3: Make the batter

In a medium bowl, whisk together 1¼ cups of all-purpose flour, 1½ teaspoons baking powder, and ¼ teaspoon salt.

In a large mixing bowl, cream ½ cup (1 stick) of softened butter with ½ cup granulated sugar until light and fluffy—about 2 to 3 minutes.

Add in two large eggs, one at a time, beating well after each addition.

Mix in 1 teaspoon of vanilla extract and 2 tablespoons of reserved pineapple juice.

Alternate adding the dry ingredients and ½ cup of milk into the butter mixture, starting and ending with dry ingredients. Mix until just combined—don’t overbeat.

Step 4: Assemble and bake

Spoon the batter over the pineapple topping in each muffin cup, filling each about ¾ full.

Place the pan in the oven and bake for 22 to 25 minutes, or until a toothpick inserted in the center of a cupcake comes out clean.

Step 5: Cool and flip

Let the cupcakes cool in the pan for 10 minutes—just enough for the sugar to settle but not harden.

Run a butter knife around the edge of each cupcake to loosen.

Place a baking sheet or cooling rack on top of the muffin pan, then quickly flip it over. Tap gently and lift the pan—each cupcake should release easily with the pineapple and cherry beautifully on top.

Let them cool a bit more before serving warm or at room temperature.

Substitutions

If you need to switch things up based on diet, allergies, or pantry availability, here are some helpful swaps:

Butter:
If you’re dairy-free, use a plant-based butter substitute. Coconut oil also works and adds a subtle tropical note.

Flour:
To make it gluten-free, use a 1:1 gluten-free baking flour blend that includes xanthan gum.

Milk:
You can use almond milk, oat milk, or any dairy-free milk you like. Whole milk gives the richest texture, but non-dairy options work just fine.

Eggs:
For an egg-free version, try using a flax egg (1 tablespoon flaxseed meal + 3 tablespoons water per egg, let sit for 5 minutes).

Cherries:
If you don’t have maraschino cherries, you can skip them or replace with a small spoonful of raspberry or cherry preserves.

The key is to keep the topping caramelized and fruity, and the cake moist and fluffy. So feel free to get creative while sticking to the spirit of the original.

Best Side Dish of Pineapple Upside Down Cupcakes

To elevate your dessert spread, consider serving these cupcakes alongside a few complementary bites:

1. Vanilla Bean Ice Cream
The cool, creamy texture contrasts beautifully with the warm caramelized topping of the cupcakes.

2. Fresh Fruit Salad
A mix of berries, kiwi, and mango adds brightness and a refreshing counterpoint to the sweet richness of the cupcakes.

3. Coconut Whipped Cream
Light, airy, and slightly nutty—this dairy-free topping makes a luxurious yet tropical addition to each cupcake plate.

Serving and Presentation Tips

When it comes to serving Pineapple Upside Down Cupcakes, the presentation can truly elevate the experience. Imagine the glossy, caramelized pineapple slices glistening atop each cupcake, crowned with a bright cherry. To make them look irresistible, here are a few tips:

Serve these cupcakes on a pretty platter or tiered cake stand to highlight their colorful tops. Arrange them with a bit of space so each one’s pineapple and cherry peek out clearly.

For an extra touch of elegance, add a small dollop of freshly whipped cream or coconut whipped cream on the side or lightly piped around the base of each cupcake. This adds creaminess and a visual contrast.

If you’re serving at a party, label them with little tropical-themed tags or toothpicks to play up the retro, island vibe. A sprinkle of finely chopped toasted coconut or a light dusting of powdered sugar can also add texture and visual appeal.

Serve these cupcakes slightly warm or at room temperature to bring out their rich, buttery flavors. Avoid chilling before serving as the caramel topping firms up and loses its luscious gloss.

Tips and Tricks to Make This Recipe Even Better

Making Pineapple Upside Down Cupcakes is simple, but a few insider tips can take your batch from good to spectacular:

Use Fresh Butter and Proper Creaming Technique: Softened butter whipped with sugar until light and fluffy creates a tender, airy crumb. Avoid using melted butter for the batter.

Reserve Pineapple Juice: Don’t discard the juice from the canned pineapple! Adding a couple of tablespoons to the batter gives a subtle pineapple undertone throughout the cupcake.

Don’t Overfill the Cups: Fill each muffin cup about three-quarters full. Overfilling can cause the topping to overflow and the cupcakes to bake unevenly.

Let the Cupcakes Cool Briefly Before Flipping: If you flip too soon, the topping might stick. Waiting about 10 minutes lets the caramel set just enough to release cleanly.

Use a Non-Stick or Well-Greased Pan: This helps the cupcakes unmold easily without damaging the delicate pineapple topping.

Experiment with Spices: Adding a pinch of cinnamon or ground ginger to the batter can add warmth and depth without overpowering the pineapple.

Choose Quality Pineapple: If possible, use good quality canned pineapple in juice (not syrup) for the best flavor and caramelization.

Common Mistakes to Avoid

Even with a straightforward recipe, there are a few pitfalls to watch out for:

Using Pineapple in Syrup Instead of Juice: The extra sugar can cause the topping to burn or become overly sticky.

Not Loosening the Cupcakes Before Flipping: Skipping the step of running a knife around the edge often leads to broken cupcakes or toppings that stay stuck in the pan.

Overbaking: Baking past the ideal time results in dry cupcakes and caramelized sugar that becomes hard instead of gooey.

Underbaking: This causes cupcakes to sink or be gummy inside.

Not Softening Butter Properly: Using cold or melted butter in the batter can affect the texture—aim for room temperature softened butter for a tender crumb.

Filling Muffin Cups Too Much or Too Little: Both can affect how the cupcakes rise and how the topping behaves.

How to Store It

Pineapple Upside Down Cupcakes are best enjoyed fresh, but if you need to store them, follow these tips:

Allow cupcakes to cool completely before storing.

Store in an airtight container at room temperature for up to 2 days to preserve the moist texture and soft topping.

If you need to store longer, refrigerate for up to 4 days. Keep in mind refrigeration can cause the caramel topping to harden slightly. Bring cupcakes back to room temperature before serving to soften.

For longer storage, freeze the cupcakes wrapped individually in plastic wrap, then placed in a freezer-safe container or bag for up to 2 months. Thaw overnight in the fridge and warm gently before serving.

Avoid storing in humid or warm environments as it can affect the caramel topping texture.

Frequently Asked Questions

Can I make these cupcakes dairy-free or vegan?
Yes! Substitute butter with coconut oil or a vegan butter alternative, and use a dairy-free milk like almond or oat. For eggs, flax eggs work well. The texture may vary slightly but the flavor will remain delicious.

Can I use fresh pineapple instead of canned?
Fresh pineapple can work but it’s less sweet and juicier, which might affect caramelization. Drain and pat dry fresh pineapple pieces well before using.

How do I prevent the cupcakes from sticking to the pan?
Make sure to grease your pan generously or use silicone muffin liners. Let cupcakes cool slightly and loosen edges with a knife before flipping.

Can I make these cupcakes ahead of time?
Yes! You can bake them a day ahead and store covered at room temperature. Just warm briefly before serving for best texture.

What can I do if I don’t have maraschino cherries?
You can omit cherries or substitute with a small spoonful of jam, fresh berries, or a small piece of candied fruit for a similar effect.

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