Mini Pineapple Upside-Down Cupcakes: A Sweet & Fruity Delight

If you love pineapple upside-down cake, these Mini Pineapple Upside-Down Cupcakes will be your new favorite treat! They’re moist, buttery, and caramelized with sweet brown sugar, juicy pineapple, and a cherry on top—all in a cute, individual-sized form.

Perfect for parties, brunch, bake sales, or a tropical-inspired dessert, these cupcakes are easy to make and guaranteed to impress.

Let’s dive into the step-by-step recipe, tips, and fun variations to make these adorable and delicious cupcakes!

Why You’ll Love These Mini Pineapple Upside-Down Cupcakes

✅ Classic Flavor in Mini Form – All the goodness of pineapple upside-down cake, but in cupcake size!
✅ Super Moist & Caramelized – The buttery brown sugar glaze makes these cupcakes irresistible.
✅ Perfect for Any Occasion – Great for parties, birthdays, summer gatherings, or a quick treat.
✅ Easy to Make – Uses simple ingredients and is beginner-friendly.
✅ Customizable – Add coconut, nuts, or even a hint of rum for a fun twist!

Ingredients You’ll Need

For the Topping

¼ cup butter, melted
½ cup brown sugar
12 maraschino cherries, halved
6 pineapple rings, cut in halves

For the Cupcake Batter

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

Step-by-Step Instructions

Step 1: Preheat & Prepare the Muffin Tin

Preheat your oven to 350°F (175°C).
Grease a 12-cup muffin tin with butter or non-stick spray.

Step 2: Make the Brown Sugar Topping

In a small bowl, mix the melted butter and brown sugar until well combined.
Spoon about 1 teaspoon of the mixture into the bottom of each muffin cup.
Place half a pineapple ring in each cup and press a maraschino cherry half in the center.

Step 3: Make the Cupcake Batter

In a medium bowl, whisk together flour, baking powder, baking soda, and salt.
In a large mixing bowl, beat the butter and sugar until light and fluffy (about 2 minutes).
Add eggs one at a time, beating after each addition.
Mix in the vanilla extract.
Gradually add the dry ingredients, alternating with pineapple juice and sour cream, mixing until smooth.

Step 4: Assemble & Bake

Spoon the cupcake batter over the pineapple mixture, filling each muffin cup about ¾ full.
Bake for 18-22 minutes, or until a toothpick inserted in the center comes out clean.
Let the cupcakes cool in the pan for 5 minutes.

Step 5: Flip & Serve!

Run a knife around the edges to loosen the cupcakes.
Place a baking sheet or plate over the muffin tin and carefully invert the cupcakes.
Let them cool slightly before serving warm or at room temperature.

Enjoy these mini pineapple upside-down cupcakes as a sweet, caramelized treat!

Serving Ideas & Pairings

🍍 With Whipped Cream – Add a dollop of freshly whipped cream on top.
🍨 With Ice Cream – Serve warm with a scoop of vanilla or coconut ice cream.
🥥 With Toasted Coconut – Sprinkle shredded coconut for extra tropical flavor.
☕ With Coffee or Tea – Perfect alongside a hot cup of coffee or fruity iced tea.

Tips for the Best Mini Pineapple Upside-Down Cupcakes

🔹 Use Room Temperature Ingredients – Ensures a smooth, even batter.
🔹 Grease the Muffin Tin Well – Helps prevent sticking when flipping the cupcakes.
🔹 Let Them Cool Slightly Before Flipping – This helps the brown sugar topping set properly.
🔹 Use Fresh Pineapple for Extra Flavor – But canned works perfectly too!
🔹 Make It Boozy – Add 1 tablespoon of rum to the batter for a fun adult twist!

Fun Variations to Try

🔥 Coconut Pineapple Cupcakes – Add ½ cup shredded coconut to the batter.
🍫 Chocolate Pineapple Cupcakes – Drizzle with melted chocolate after flipping.
🥜 Nutty Pineapple Upside-Down Cupcakes – Sprinkle chopped pecans or walnuts in the brown sugar topping.
🍹 Piña Colada Cupcakes – Add a splash of coconut extract and top with whipped cream.
🍓 Berry Pineapple Cupcakes – Swap cherries for strawberries or raspberries.

Frequently Asked Questions

Can I Make These Ahead of Time?

Yes! Store them in an airtight container at room temperature for up to 2 days, or refrigerate for up to 5 days.

Can I Freeze Pineapple Upside-Down Cupcakes?

Absolutely! Freeze in a single layer for up to 3 months. Thaw at room temperature before serving.

Do I Have to Use Muffin Liners?

No, but greasing the muffin tin well is important to prevent sticking.

What If I Don’t Have Pineapple Juice?

You can substitute with orange juice or apple juice for a similar fruity flavor.

Final Thoughts

These Mini Pineapple Upside-Down Cupcakes are a fun, tropical twist on the classic cake, perfect for any occasion. With caramelized pineapple, a hint of vanilla, and a soft, buttery cake, they’re irresistibly delicious and easy to make.

Try this quick and easy recipe today, and enjoy a bite-sized tropical treat that will impress everyone!