Whether you’re hosting a lively summer gathering, looking for a nostalgic dessert, or just craving a bite of something sweet and satisfying, these cupcakes will steal the show. No slicing, no messy serving—just grab, flip, and indulge!

Why You’ll Fall in Love with These Pineapple Upside-Down Cupcakes

✔️ A Tropical Flavor Explosion – Caramelized pineapple and rich vanilla cake create a perfect harmony of sweet, buttery goodness.

✔️ No-Fuss Serving – Unlike traditional cakes, these require zero slicing. Just pop them out of the pan and they’re ready to impress.

✔️ Stunning Presentation – The glossy fruit topping makes these cupcakes look like a work of art straight out of a bakery display.

✔️ Perfect for Any Occasion – Ideal for birthdays, brunches, holidays, or a fun weekend baking project.

Ingredients You’ll Need

For the Caramelized Pineapple Topping:

½ cup unsalted butter, melted
1 cup packed light brown sugar
24 maraschino cherries, stems removed
1 ½ cups pineapple chunks, well-drained

For the Cupcake Batter:

1 ¾ cups all-purpose flour
1 ½ teaspoons baking powder
½ teaspoon baking soda
¼ teaspoon salt
½ cup unsalted butter, softened
1 cup granulated sugar
2 large eggs
1 teaspoon vanilla extract
¾ cup buttermilk

Step-by-Step Guide to Baking Perfection

Step 1: Prep the Muffin Tin & Topping Preheat your oven to 350°F (175°C). Generously grease a 12-cup muffin tin with butter or nonstick spray to prevent sticking.

Sprinkle 1 tablespoon of brown sugar into the bottom of each muffin cup, followed by a drizzle of melted butter. Place a pineapple chunk over the sugar mixture, then press a maraschino cherry right in the center.

Step 2: Whip Up the Cupcake Batter In a medium bowl, whisk together the flour, baking powder, baking soda, and salt. Set aside.

In a separate large bowl, beat the softened butter and granulated sugar until light and fluffy—about 2 minutes. Add eggs one at a time, mixing well after each. Stir in vanilla extract.

Alternately add the dry ingredients and buttermilk to the wet mixture, beginning and ending with the dry ingredients. Stir just until combined—do not overmix!

Step 3: Assemble & Bake Spoon the cupcake batter over the pineapple and cherries, filling each muffin cup about ¾ full. Bake for 18-22 minutes, or until a toothpick inserted into the center comes out clean.

Let the cupcakes cool for about 5 minutes in the pan, then carefully invert them onto a wire rack while still warm. The caramelized topping will create a glossy, irresistible finish.

Expert Tips for the Best Results

✔️ Grease Generously – A well-greased muffin tin ensures the cupcakes flip out beautifully.

✔️ Drain Pineapple Well – Excess juice can make the sugar mixture too runny.

✔️ Invert While Warm – Don’t wait too long before flipping, or the sugar will set and stick.

✔️ Use Buttermilk – It adds richness and keeps the cupcakes moist.

✔️ Cool Completely Before Storing – This prevents excess moisture from making them soggy.

Frequently Asked Questions (FAQ)

🔸 Do Pineapple Upside-Down Cupcakes Need to Be Refrigerated? Yes! Because of the fresh fruit topping, store them in an airtight container in the fridge for up to 3 days.

🔸 Can I Use Fresh Pineapple? Absolutely! Just cut into small chunks and drain well to avoid excess moisture.

🔸 Can I Use Cupcake Liners? Nope! Baking directly in the tin allows for that signature upside-down effect when flipped.

🔸 Can These Be Made in Advance? Yes! Bake them a day ahead and refrigerate. Warm slightly before serving for the best taste.

🔸 What if I Don’t Have Buttermilk? No worries! Mix ¾ cup milk with 1 teaspoon of lemon juice or vinegar. Let sit for 5 minutes before using.

🔸 How Do I Reheat Them? Microwave for 10-15 seconds for a quick warm-up, or place in a 300°F (150°C) oven for 5-7 minutes.

Final Thoughts: A Nostalgic Treat with a Modern Twist

Pineapple upside-down cupcakes are more than just a dessert; they’re a bite-sized journey into the past, delivering flavors of nostalgia with a fresh, tropical spin. Whether you’re an experienced baker or a kitchen newbie, these cupcakes are an easy, rewarding treat that will leave everyone asking for more.

Go ahead—take a trip to the tropics, one sweet bite at a time! 🍍✨