Mini Pineapple Upside-Down Cupcakes Recipe

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If you love the tropical taste of pineapple upside-down cake, you’re going to be obsessed with these Mini Pineapple Upside-Down Cupcakes. These bite-sized treats have all the classic flavor you love—caramelized pineapple, bright maraschino cherries, and soft, buttery cake—in a personal-sized portion perfect for parties, picnics, or a sweet snack.

Baked in a muffin tin, these little cupcakes are not only adorable, but they also bake faster and serve easier than a traditional cake. Best of all, there’s no slicing required! Flip them out of the pan for a stunning, glossy presentation that makes them look as good as they taste.

Why You’ll Love This Mini Pineapple Upside-Down Cupcakes Recipe

These cupcakes are a fun twist on a classic dessert. They’re quick to make, easy to serve, and always get a ton of compliments. You’ll love the balance of sweet pineapple and cherry on top of moist vanilla cake, all caramelized to perfection with a buttery brown sugar glaze.

Perfect for gatherings or gifting, they’re portable, portioned, and don’t need any frosting or extra decoration. That makes them one of the easiest and most impressive desserts to bring to any event.

What Kind of Pineapple Should I Use?

Canned pineapple rings work best for this recipe because they’re uniform in size and soft enough to caramelize quickly. If using whole rings, you can cut them into smaller pieces to fit each muffin cup. Pineapple tidbits can also work, but they won’t give the same iconic look. Always drain them well to avoid soggy bottoms.

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Ingredients for the Mini Pineapple Upside-Down Cupcakes Recipe

Every layer in these cupcakes—from the fruity topping to the tender cake—adds something special. Here’s why each ingredient matters:

• Canned pineapple rings – Provide the tropical sweetness and signature upside-down look. Slice them to fit the muffin tin.
• Maraschino cherries – Bright, sweet, and decorative, these go right in the center of the pineapple.
• Unsalted butter – Used to create the rich brown sugar caramel that coats the top.
• Brown sugar – Melts into a delicious syrup that soaks into the fruit and cake.
• Granulated sugar – Sweetens the cake portion.
• Eggs – Give structure and richness to the cake batter.
• Vanilla extract – Enhances the flavor and gives warmth to the cake.
• All-purpose flour – Forms the base of the cupcake batter.
• Baking powder – Helps the cupcakes rise and stay light.
• Salt – Balances out the sweetness.
• Milk – Adds moisture and brings everything together.

How To Make the Mini Pineapple Upside-Down Cupcakes Recipe

Step 1: Prepare the Topping

Preheat your oven to 350°F (175°C). Grease a 12-cup muffin tin. In a small bowl, mix melted butter with brown sugar and spoon about a teaspoon into the bottom of each muffin cup. Add a cherry in the center, then arrange a small pineapple slice or piece around it.

Step 2: Make the Cake Batter

In a bowl, whisk together flour, baking powder, and salt. In another bowl, beat butter and granulated sugar until fluffy. Add eggs and vanilla, mixing well. Slowly mix in the dry ingredients, alternating with milk until just combined.

Step 3: Assemble the Cupcakes

Spoon the batter evenly into each muffin cup over the pineapple and cherry layer, filling about ¾ full.

Step 4: Bake and Cool

Bake for 20–25 minutes or until a toothpick comes out clean. Let the cupcakes cool in the tin for 5 minutes.

Step 5: Flip and Serve

Run a knife around the edges and invert the cupcakes onto a baking sheet or platter. Serve warm or at room temperature.

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Serving and Storing Mini Pineapple Upside-Down Cupcakes

This recipe makes 12 mini cupcakes, ideal for parties, potlucks, or any occasion where you want a pretty, easy-to-serve dessert. Serve them slightly warm or at room temperature, and don’t forget a scoop of vanilla ice cream on the side for extra indulgence.

To store leftovers, let the cupcakes cool completely and place them in an airtight container. Keep them in the refrigerator for up to 4 days. Reheat gently in the microwave for about 10–15 seconds if desired.

What to Serve With Mini Pineapple Upside-Down Cupcakes?

These cupcakes are sweet and fruity, so they pair well with light, fresh sides or creamy accompaniments.

Vanilla Ice Cream

The contrast of warm cupcakes and cold vanilla ice cream is an unbeatable combo.

Coconut Whipped Cream

Add a tropical twist by topping each cupcake with coconut-infused whipped cream.

Fresh Berries

Serve a small bowl of fresh raspberries or strawberries on the side for color and freshness.

Espresso or Coffee

Balance the sweetness with a rich cup of coffee or espresso.

Sparkling Water or Lemonade

For a non-dessert pairing, serve with something bubbly and refreshing.

Chocolate Sauce

Drizzle a little chocolate sauce over the cupcakes for a fun fusion of flavors.

Yogurt Parfaits

Turn them into a brunch-worthy dessert with a side of fruit and yogurt parfaits.

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Frequently Asked Questions

1. Can I use fresh pineapple instead of canned?
Yes! Just slice it thinly and make sure it’s soft and sweet. Canned is more consistent and convenient, but fresh works great too.

2. Do I need cupcake liners?
No liners needed—just grease the muffin tin well so the cupcakes flip out easily after baking.

3. Can I make these in advance?
Absolutely. Make them a day ahead and store them in the fridge. Reheat gently or serve at room temp.

4. What if the topping sticks to the pan?
Let the cupcakes rest for 5 minutes after baking, then run a knife around the edges and flip. If any topping stays behind, just scoop it out and place it back on top.

5. Can I freeze these?
Yes! Wrap them tightly and freeze for up to 1 month. Thaw in the fridge and warm up before serving.

Save This Pin For Later

📌 Save this recipe to your Pinterest dessert board so you can come back to it any time.

Let me know in the comments if you added a splash of rum or used fresh fruit! I love seeing your creative twists.

Explore more delicious mini desserts and classic sweet bites on Tanya Recipes on Pinterest—perfect for any occasion!

Conclusion

Mini Pineapple Upside-Down Cupcakes are the perfect combination of nostalgic flavor and modern presentation. With their caramelized fruit topping and buttery soft cake, they’re a beautiful and delicious treat that’s sure to impress. Whether for a special event or just a sweet craving, these little cakes deliver big-time flavor in every bite.

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