Pineapple Upside Down Cupcakes

There’s something undeniably nostalgic about pineapple upside down cake. It’s the kind of dessert that brings back memories of Sunday potlucks, family barbecues, or grandparent’s kitchens where the scent of caramelized pineapple and warm butter filled the air.

But what if we could take that old-fashioned charm and turn it into something more portable, more party-friendly, and just as delightful?

That’s exactly why I created these Pineapple Upside Down Cupcakes—single-serve versions of the classic dessert that don’t compromise on flavor.

They’re easy to serve, make a beautiful presentation on a tray, and are beloved by both kids and adults alike.

If you’ve ever hesitated to make a full upside-down cake because of slicing and plating logistics, these cupcakes solve that problem perfectly.

Why I Love This Recipe

These cupcakes aren’t just adorable—they’re loaded with flavor, texture, and visual appeal. What makes them stand out is the perfect harmony of rich brown sugar caramel, juicy pineapple, and soft, buttery cake.

Each cupcake is a self-contained bite of golden sweetness, with that gorgeous pineapple ring and vibrant cherry nestled right on top.

The beauty lies in their simplicity. There’s no need for frosting because the caramelized fruit topping speaks for itself. Plus, they bake faster than a traditional cake and cool quickly, meaning you can enjoy them sooner.

Whether you’re making a batch for a summer picnic, a birthday party, or just a midweek treat, they’re sure to impress.

Even better? These cupcakes keep well, travel well, and offer the joy of pineapple upside down cake in the palm of your hand.

Ingredients for Pineapple Upside Down Cupcakes

Here’s everything you’ll need to make these beauties come to life:

For the topping (the “upside-down” part):
This is what gives these cupcakes their signature look and flavor.

• Canned pineapple rings in juice (not syrup)
• Maraschino cherries
• Brown sugar (light or dark works)
• Unsalted butter

For the cupcake batter:
A light, moist cake base that complements the topping without overpowering it.

• All-purpose flour
• Baking powder
• Baking soda
• Salt
• Unsalted butter (softened)
• Granulated sugar
• Large eggs
• Sour cream or plain Greek yogurt
• Whole milk
• Pure vanilla extract

Optional: a splash of pineapple juice from the can for extra flavor

This combination of ingredients ensures the cupcakes have both a tender crumb and a buttery richness that contrasts beautifully with the caramelized fruit.

How Much Time Will You Need?

The process is quick and manageable, even if you’re baking with little ones.

Here’s the breakdown:

• Prep Time: 20 minutes
• Bake Time: 20–25 minutes
• Cooling Time: 15–20 minutes

So from start to finish, you’re looking at just about one hour. You can even make these a day in advance.

How to Make This Pineapple Upside Down Cupcakes

Follow these steps closely to get perfect results every time.

Step 1: Preheat and Prep

Start by preheating your oven to 350°F (175°C).

Grease a standard 12-cup muffin tin generously with butter or nonstick spray. You can use liners, but I recommend going without for that beautiful pineapple top to shine.

Step 2: Prepare the Topping

Melt ¼ cup of butter and divide evenly among the 12 muffin cups.

Sprinkle 1 tablespoon of brown sugar into each cup over the melted butter.

Cut pineapple rings to fit the muffin cups—usually cutting them in halves or thirds works best.

Place a piece of pineapple in each muffin cup and nestle a maraschino cherry in the center.

Set the pan aside while you prepare the batter.

Step 3: Make the Cupcake Batter

In a medium bowl, whisk together:

• 1 ½ cups all-purpose flour
• 1 tsp baking powder
• ½ tsp baking soda
• ¼ tsp salt

In a separate large bowl, beat together:

• ½ cup unsalted butter (softened)
• ⅔ cup granulated sugar

Cream until light and fluffy—about 2 minutes. Add:

• 2 large eggs, one at a time
• 1 tsp vanilla extract

Mix until combined.

Add the dry ingredients to the wet, alternating with:

• ½ cup sour cream (or plain Greek yogurt)
• ¼ cup whole milk

Stir until the batter is smooth and lump-free. Don’t overmix.

Optional: Add 1–2 tablespoons of pineapple juice from the can for extra tang and depth.

Step 4: Assemble and Bake

Spoon the batter evenly over the pineapple in each muffin cup. Fill to about ¾ full.

Place the pan in the oven and bake for 20–25 minutes, or until the tops are golden and a toothpick inserted in the center comes out clean.

Let the cupcakes cool in the pan for 10–15 minutes. Then run a knife around the edges and carefully invert the pan onto a baking sheet or wire rack.

Let them fall out gently—some pineapple pieces may stick, so nudge them back into place if needed.

Step 5: Cool and Serve

Allow the cupcakes to cool slightly before serving. They can be served warm or at room temperature.

Substitutions

This recipe is flexible and forgiving. Here are some smart swaps if you’re missing an ingredient or want to tweak the flavor:

• Flour: You can use cake flour for a lighter crumb or gluten-free flour blends if needed.
• Butter: If you want a dairy-free version, swap in a high-quality vegan butter substitute.
• Sour Cream: Plain Greek yogurt or even buttermilk will work just as well, maintaining the tang and moisture.
• Cherries: You can use fresh cherries (pitted) or dried ones rehydrated in juice if you prefer less sweetness.
• Sugar: Brown sugar brings the best caramel notes, but coconut sugar offers a more natural option.

Best Side Dishes for Pineapple Upside Down Cupcakes

These cupcakes can hold their own, but if you want to pair them with something complementary, try these:

1. Coconut Whipped Cream – A light and tropical topping that adds creaminess without heaviness.
2. Fruit Salad with Mint and Lime – A fresh, tangy contrast that brightens up dessert time.
3. Iced Chai Latte – Warm spices with creamy notes pair beautifully with the tropical flavors of the cupcakes.

Serving and Presentation Tips

Pineapple Upside Down Cupcakes already look stunning thanks to their glistening fruit tops, but a little finesse in presentation can make them even more eye-catching.

Here are a few ideas to elevate the look:

• Serve on a white or pastel-colored platter to make the golden tops and ruby red cherries pop.
• Garnish with a fresh mint leaf placed beside the cherry—it adds color contrast and a hint of freshness.
• Dust with a fine sprinkle of powdered sugar around the base (not the top!) for a subtle touch of elegance.
• Serve slightly warm with a scoop of vanilla bean ice cream if you want to transform it into a plated dessert.

For parties or potlucks, you can display them in individual cupcake wrappers after baking and inverting—this keeps things neat and easy for guests to grab.

Tips and Tricks to Make This Recipe Better

Want to get bakery-style results? These tips make all the difference:

• Grease generously. Use softened butter or baking spray with flour to coat each muffin tin thoroughly. This ensures the fruit topping releases easily when inverted.
• Use room temperature ingredients. This includes butter, eggs, and sour cream. It helps the batter emulsify smoothly, resulting in a tender crumb.
• Dry the pineapple slices slightly. Blot the pineapple rings with paper towels before placing them in the tin. This prevents excess moisture from making the cupcakes soggy.
• Don’t overfill the muffin cups. Stick to about ¾ full, even if you’re tempted to go higher. Overflowing batter will ruin the shape of the finished cupcakes.
• Invert with confidence. Let the cupcakes rest for about 10–15 minutes, then invert them in one quick motion. Hesitating can cause the fruit to stick.

Hook: These small changes are what take your cupcakes from good to “how did you make these!?”

Common Mistakes to Avoid

Even simple recipes can go sideways if you’re not careful. Avoid these pitfalls for best results:

• Using syrup-packed pineapple. Always opt for pineapple packed in juice. Syrup adds too much sweetness and can make the topping gummy.
• Skipping the cooling period before inverting. If you flip too soon, the topping may be too soft and slide off. Too late, and it might stick.
• Overmixing the batter. This creates dense cupcakes. Mix until just combined.
• Undercooking. A gooey bottom might sound appealing, but if the centers aren’t fully baked, they won’t hold up when inverted.
• Not checking your oven temperature. A too-hot oven can caramelize the sugar too quickly, leading to a burnt topping. Use an oven thermometer if unsure.

How to Store It

These cupcakes store well, but how you store them makes a difference.

Room Temperature:
Store in an airtight container at room temperature for up to 2 days. Place parchment between layers to prevent sticking.

Refrigerator:
If you want to keep them longer, refrigerate for up to 5 days. Let them come to room temp before serving, or warm slightly in the microwave.

Freezer:
Yes, you can freeze them! Wrap each cupcake tightly in plastic wrap and place in a zip-top bag. Freeze for up to 2 months. Thaw overnight in the fridge and warm gently before serving.

Note: The topping may lose some of its shine after freezing, but the flavor remains fantastic.

FAQ

1. Can I make these in a jumbo muffin tin?
Yes! Just adjust the baking time to around 28–32 minutes and use larger pineapple rings or slices to fit the bigger cups.

2. Can I use fresh pineapple instead of canned?
Absolutely. Just slice it thinly and use small rounds or half-moons. You may need to soften the pineapple slightly in a pan with a little butter to ensure it caramelizes well.

3. What can I use instead of cherries?
Try a dried apricot, raspberry, or even a pecan half for a nutty twist.

4. Can I make these ahead of time?
Yes. Bake the night before and store in an airtight container. Warm them gently before serving for best texture and flavor.

5. Are these cupcakes suitable for vegetarians?
Yes, they are! All ingredients are vegetarian-friendly. Just double-check the maraschino cherry brand you use to ensure no additives that aren’t.

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