Mini Pineapple Upside-Down Cupcakes

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If you’re looking for a dessert that brings sunshine to the table, these Mini Pineapple Upside-Down Cupcakes are a showstopper. Each little cake is crowned with a glistening slice of caramelized pineapple and a vibrant maraschino cherry, baked to golden perfection. The combination of juicy fruit, sticky brown sugar, and moist vanilla cake makes every bite a tropical dream.

Perfect for parties, potlucks, or just a sweet afternoon treat, these cupcakes are as fun to eat as they are to make. Plus, their individual serving size makes them ideal for sharing (or not sharing!). Whether you’re a longtime fan of the classic pineapple upside-down cake or trying it for the first time, this mini version will win you over instantly.

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

These cupcakes are incredibly easy to make with pantry-friendly ingredients, yet they look and taste like something from a bakery. The gooey caramelized topping paired with a buttery vanilla base creates a delicious contrast in texture and flavor. They bake up beautifully and pop right out of the muffin tin, revealing their stunning tops with no frosting required.

Best of all? You get all the nostalgic flavor of the traditional upside-down cake with a modern, portable twist.

What Kind of Pineapple Should I Use?

For best results, use canned pineapple slices packed in juice. They’re convenient, consistent in size, and easy to work with. Be sure to drain the slices well and cut them into halves or smaller circles to fit perfectly into the bottom of each muffin cup. If you prefer fresh pineapple, just make sure it’s cut thinly and uniformly for even caramelization.

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Ingredients for the Mini Pineapple Upside-Down Cupcakes

Each ingredient in this recipe plays an important role in flavor, texture, and presentation. Here’s what you’ll need:

• Pineapple Slices: The star of the show. Choose canned pineapple rings in juice, then cut them to fit the muffin cups.
• Maraschino Cherries: These sweet, ruby-red cherries sit on top of the pineapple and give that signature look and pop of color.
• Unsalted Butter: Used both in the cake batter and to create that rich, caramel-like base with the brown sugar.
• Brown Sugar: When baked under the pineapple, it melts into a gooey, buttery topping.
• Granulated Sugar: Sweetens the cupcake batter just right.
• Eggs: Help to bind the batter and add richness.
• All-Purpose Flour: Forms the base of the cupcake structure.
• Baking Powder: Gives the cupcakes their light, fluffy texture.
• Salt: Balances the sweetness and enhances the other flavors.
• Vanilla Extract: Adds warmth and depth to the flavor profile.
• Milk: Keeps the cupcakes moist and tender.

How To Make the Mini Pineapple Upside-Down Cupcakes

Step 1: Prepare the Muffin Tin

Grease a standard 12-cup muffin tin well. Place 1/2 tablespoon of melted butter and 1 tablespoon of brown sugar into the bottom of each cup. Add a piece of pineapple and a cherry in the center.

Step 2: Mix the Wet Ingredients

In a mixing bowl, cream together the remaining butter and granulated sugar until light and fluffy. Beat in the eggs one at a time, then add vanilla extract.

Step 3: Combine the Dry Ingredients

In another bowl, whisk together the flour, baking powder, and salt. Gradually add the dry mixture to the wet, alternating with milk, until just combined.

Step 4: Fill the Muffin Cups

Spoon the batter evenly over the fruit in each muffin cup, filling each about 3/4 full.

Step 5: Bake and Invert

Bake at 350°F (175°C) for 20–25 minutes or until a toothpick inserted into the center comes out clean. Let cool in the tin for 5 minutes, then carefully invert onto a wire rack. Let the caramel drip over the tops for that classic upside-down look.

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How to Serve and Store These Mini Pineapple Upside-Down Cupcakes

These delightful mini cakes are best served slightly warm or at room temperature, when the caramel topping is gooey and the pineapple is juicy. They make a stunning dessert for gatherings, and their small size makes them easy to serve on a platter. This recipe yields 12 cupcakes and is perfect for feeding 6–8 people.

To store, place them in an airtight container at room temperature for up to 2 days. For longer storage, refrigerate them for up to 5 days. You can reheat briefly in the microwave to soften the topping again before serving. If you’d like to freeze them, wrap each cupcake tightly in plastic wrap and store in a freezer-safe bag for up to a month. Thaw in the fridge overnight and warm gently before enjoying.

What to Serve With Mini Pineapple Upside-Down Cupcakes?

Fresh Whipped Cream

A dollop of lightly sweetened whipped cream makes the perfect, airy contrast to the rich caramelized topping.

Vanilla Ice Cream

The cool creaminess of vanilla ice cream complements the warm cupcake beautifully—especially when served fresh out of the oven.

Coconut Flakes

Toasted coconut sprinkled on top adds a lovely tropical crunch and aroma.

Caramel Drizzle

Enhance the presentation and flavor with a drizzle of extra caramel or butterscotch sauce.

Fresh Mint Leaves

Add a fresh and colorful garnish with a few mint leaves on the side.

Tropical Fruit Salad

A bowl of chopped mango, kiwi, and papaya pairs wonderfully and keeps the dessert light.

Coffee or Espresso

Balance the sweetness with a robust coffee or espresso to finish off your meal.

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Frequently Asked Questions

Can I make these cupcakes ahead of time?

Absolutely! You can make them a day in advance. Just let them cool completely, then store them in an airtight container at room temperature. For the best texture, reheat them for a few seconds in the microwave before serving.

Can I use fresh pineapple instead of canned?

Yes, you can! Just slice the pineapple very thin and make sure to remove any tough core pieces. Fresh pineapple may release more juice, so lightly pat the slices dry with a paper towel before using.

Why did my cupcakes stick to the muffin tin?

Sticking can happen if the muffin tin isn’t greased well or if the cupcakes are left in the tin too long after baking. Make sure to grease generously and invert them within 5 minutes of removing them from the oven.

Can I make these gluten-free?

Yes, just substitute your favorite gluten-free all-purpose flour blend in a 1:1 ratio. Ensure that your other ingredients, like baking powder, are certified gluten-free as well.

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Save this recipe to your Pinterest dessert board so you can come back to it any time.
And let me know in the comments how yours turned out. Did you use fresh pineapple or canned? Did you sneak in some coconut?
I love hearing how others make these recipes their own. Questions are welcome too, let’s help each other bake smarter.

Explore more delicious ideas on my Meals We Share By Sally Pinterest — I share daily recipes and sweet treats you’ll love!

Conclusion

These Mini Pineapple Upside-Down Cupcakes are a sunny, retro-inspired treat with a fresh twist. They’re easy to make, beautiful to serve, and bursting with flavor in every bite. Whether you’re baking for a crowd or treating yourself, this is a recipe that delivers happiness in cupcake form.

Give them a try and bring a little tropical joy into your kitchen!

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