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Why You’ll Love This Recipe

Perfect for Any Occasion – These cupcakes are great for parties, bake sales, or just a fun weekend treat.
Classic Flavor in a Mini Form – Get the delicious taste of pineapple upside-down cake in an easy-to-serve, individual cupcake.
Irresistible Caramelized Topping – The brown sugar and butter create a rich caramel layer that pairs perfectly with juicy pineapple.
Moist and Fluffy – The cupcakes are light and soft, thanks to the perfect balance of buttermilk and pineapple juice.
No Special Equipment Needed – All you need is a muffin tin and a few pantry staples!
For a fresh, fruity side dish to pair with your cupcakes, try making a homemade fruit salad!

Ingredients You’ll Need

Pineapple upside-down cupcakes with caramelized pineapple and cherries, cooling on a wire rack. One cupcake is cut open, showing its moist texture.

For the Topping:

¼ cup unsalted butter, melted
½ cup brown sugar, packed
6 pineapple rings (halved or quartered)
12 maraschino cherries

For the Cupcake Batter:

1 ½ cups all-purpose flour
1 ½ teaspoons baking powder
¼ teaspoon salt
½ cup unsalted butter, softened
¾ cup granulated sugar
2 large eggs
1 teaspoon vanilla extract
½ cup buttermilk
¼ cup of pineapple juice (reserved from the canned pineapple)

Looking for another tropical treat? Try this passion fruit juice recipe for a refreshing pairing!

Step-by-Step Instructions

Step-1: Get the Muffin Tin Ready

Preheat the oven to 350°F (175°C) to ensure even baking
Generously grease a 12-cup muffin tin or line it with cupcake liners for easy removal.

Step-2: Make the Caramelized Topping

In a small bowl, mix melted butter and brown sugar until fully blended.
Place approximately a teaspoon of the rich mixture into the bottom of each muffin cup.
Place a pineapple slice over the sugar mixture, then nestle a maraschino cherry in the center for a pop of color and flavor.

Step-3: Mix the Cupcake Batter

Combine the flour, baking powder, and salt in a medium bowl, whisking until well blended.
Using a large bowl, cream the butter and sugar until pale and fluffy.
Add the eggs one at a time, mixing well after each addition, then blend in the vanilla extract for enhanced flavor.
Gradually fold in the dry ingredients, alternating with buttermilk and pineapple juice, stirring gently until just combined. Be careful not to overmix to maintain a soft cupcake texture.

Step-4: Assemble and Bake

Portion out the batter equally into the muffin cups, ensuring each is about ¾ full.
Bake in the preheated oven for 18-22 minutes, checking for doneness with a toothpick.
Let the cupcakes cool for about five minutes, then carefully flip them onto a wire rack while still warm. This will allow the caramelized topping to release smoothly.

Variations to Try

Coconut Infusion – Add ¼ cup shredded coconut to the batter for a tropical twist.
Spiced Version – Mix in ½ teaspoon cinnamon for a warm, comforting flavor.
Boozy Twist – Substitute 1 tablespoon of rum for some of the pineapple juice for an extra kick.
Healthier Option – Swap Greek yogurt for buttermilk and coconut sugar for brown sugar.

Serving Suggestions

Pair with Ice Cream – Enjoy warm with a scoop of vanilla or coconut ice cream.
With Whipped Cream – A dollop of whipped cream balances the caramelized topping beautifully.
Paired with a Tropical Drink – These cupcakes go great with a Passion Fruit Juice (Try this recipe).
As a Brunch Dessert – Add them to a fruit platter for a fun breakfast treat (Check out how to make a fruit platter).

Looking for more fruity treats? Try this strawberry crunch cake for another delicious dessert option!

FAQs

Do pineapple upside-down cupcakes need to be refrigerated?

Proper Storage – Store in an airtight container at room temperature for up to 2 days. If keeping longer, refrigerate for up to 5 days and allow to reach room temperature before serving for optimal taste.

What is the trick to flipping pineapple upside-down cupcakes?

Removing the Cupcakes – Let the cupcakes cool for around 5 minutes before turning them out. If they stick, gently run a knife around the edges. Position a plate or wire rack over the muffin tin and invert with a swift motion.

What type of cake mix can I use for pineapple upside-down cupcakes?

A yellow cake mix or vanilla cake mix works best because of their rich, buttery flavors. A spice cake mix can also be used for a warm, spiced variation. If using a mix, reduce the liquid slightly to balance the added pineapple juice.

Do you flip a pineapple upside-down cupcake when it’s hot or cold?

Flip them while they’re still warm (after about 5 minutes of cooling). If they cool completely, the caramelized topping may stick to the pan, making them harder to remove.

More About Pineapple Upside-Down Cupcakes

If you’re looking for healthier ingredient swaps or dietary alternatives, EatingWell offers great insights on making desserts more nutritious without compromising flavor.

Pineapple Upside-Down Cupcakes That Make You Smile