Who doesn’t love the tropical flavor and sweet nostalgia of pineapple upside-down cake? Now imagine that deliciousness, but in cute, portable cupcake form! These Pineapple Upside-Down Cupcakes combine a buttery caramelized topping with moist, fluffy vanilla cake. Each bite is a perfect balance of tangy pineapple, sweet cherries, and buttery cake.

Whether you’re hosting a party, looking for an easy dessert, or just want a fun way to enjoy a classic, these cupcakes are a guaranteed hit!

Why You’ll Love These Pineapple Upside-Down Cupcakes

• Portion-perfect: No slicing or serving needed—just grab and enjoy.
• Rich and flavorful: The caramelized pineapple topping paired with moist cake is irresistible.
• Great for any occasion: Perfect for birthdays, picnics, or just because.
• Easy to make: With simple ingredients and straightforward steps, anyone can bake these!

Ingredients for Pineapple Upside-Down Cupcakes

For the Topping

• 1/4 cup unsalted butter, melted
• 1/2 cup brown sugar, packed
• 1 can (20 oz) pineapple rings, drained and cut into small chunks
• Maraschino cherries, halved

For the Cupcakes

• 1 1/2 cups all-purpose flour
• 1 1/2 tsp baking powder
• 1/4 tsp salt
• 1/2 cup unsalted butter, softened
• 1 cup granulated sugar
• 2 large eggs
• 1 tsp vanilla extract
• 1/2 cup pineapple juice (reserved from the canned pineapple)
• 1/4 cup whole milk

Tools You’ll Need

• Muffin tin (12-cup capacity)
• Non-stick spray or cupcake liners
• Mixing bowls
• Whisk or electric mixer
• Spoon for assembling the topping

How to Customize Your Cupcakes

Want to add your own twist? Here are some ideas:

• Add coconut: Sprinkle shredded coconut into the batter or topping for extra tropical flavor.
• Use a spice blend: Add a pinch of cinnamon or nutmeg to the batter for warmth.
• Swap the cherries: Use fresh raspberries or candied ginger for a fun alternative.
• Make it boozy: Replace part of the pineapple juice with rum for a pina colada vibe.

Step-by-Step Instructions

Step 1: Preheat the Oven

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

Step 2: Prepare the Topping

In a small bowl, mix the melted butter and brown sugar until combined. Spoon about 1 teaspoon of the mixture into the bottom of each muffin cup. Add a few small chunks of pineapple and half a maraschino cherry to each cup, arranging them neatly.

Step 3: Mix the Dry Ingredients

In a medium bowl, whisk together the flour, baking powder, and salt. Set aside.

Step 4: Cream the Butter and Sugar

In a large bowl, use an electric mixer to cream the softened butter and granulated sugar until light and fluffy (about 2–3 minutes).

Step 5: Add Eggs and Vanilla

Beat in the eggs, one at a time, followed by the vanilla extract. Mix until well combined.

Step 6: Combine Wet and Dry Ingredients

Add the dry ingredients to the butter mixture in three additions, alternating with the pineapple juice and milk. Begin and end with the dry ingredients, mixing just until combined.

Step 7: Assemble the Cupcakes

Spoon the batter over the pineapple topping in each muffin cup, filling each cup about two-thirds full. Smooth the tops with a spoon or spatula.

Step 8: Bake

Bake in the preheated oven for 20–25 minutes, or until a toothpick inserted into the center of a cupcake comes out clean.

Step 9: Cool and Invert

Allow the cupcakes to cool in the pan for about 5 minutes. Run a knife around the edges to loosen, then carefully invert the cupcakes onto a baking sheet or platter while they’re still warm. Let them cool completely before serving.

Tips for Perfect Pineapple Upside-Down Cupcakes

• Don’t overfill the cups: Leave enough room for the batter to rise without spilling over.
• Work quickly when inverting: The topping sticks best when the cupcakes are warm.
• Grease the pan well: This prevents the caramelized topping from sticking to the pan.
• Use fresh pineapple: If you prefer, substitute canned pineapple with fresh pineapple for a brighter flavor.

What to Serve with Pineapple Upside-Down Cupcakes

These cupcakes are delightful on their own, but they pair wonderfully with:

• Vanilla ice cream: A scoop on the side makes this dessert even more indulgent.
• Whipped cream: Add a dollop of lightly sweetened whipped cream for extra flair.
• Coffee or tea: The tropical flavors pair beautifully with a hot beverage.

How to Store Pineapple Upside-Down Cupcakes

• Room Temperature: Store in an airtight container for up to 1 day.
• Refrigerator: These cupcakes keep well in the fridge for 3–4 days. Bring to room temperature or warm slightly before serving.
• Freezer: Wrap individually and freeze for up to 2 months. Thaw in the fridge overnight before enjoying.

Frequently Asked Questions

Can I make these cupcakes ahead of time?

Yes! You can bake them a day ahead and store them in the fridge. Warm slightly before serving for the best texture.

What if I don’t have a muffin tin?

You can use ramekins or bake as a small cake in a 9-inch round pan. Adjust the baking time as needed.

Can I use cake mix instead of making the batter from scratch?

Absolutely! A boxed yellow or vanilla cake mix works perfectly for a shortcut version.

Why You’ll Love These Cupcakes

These Pineapple Upside-Down Cupcakes are as fun to make as they are to eat. The combination of buttery caramelized fruit and soft cake is a classic for good reason. Plus, their individual portions make them perfect for sharing—or keeping all to yourself!

If you make this recipe, I’d love to see how they turned out! Share your photos on Pinterest or leave a comment below.

More Delicious Desserts to Try:

• Mini Cheesecake Bites
• Lemon Bars with Shortbread Crust
• Banana Bread Muffins

Nutritional Information (Per Cupcake):

• Calories: 220
• Carbs: 35g
• Fat: 9g
• Protein: 3g

Enjoy these delightful little cakes, one sweet bite at a time! 🍍