Name: Pineapple Upside Down Cupcakes
Prep time: 15 min
Cook time: 25 min
Total time: 40 min
Ingredients: 1/4 cup unsalted butter, melted; 1/2 cup brown sugar, packed; 12 maraschino cherries, halved; 1 cup pineapple chunks (or crushed pineapple, drained); 1 cup all-purpose flour; 1/2 cup granulated sugar; 1/2 teaspoon baking powder; 1/4 teaspoon baking soda; 1/4 teaspoon salt; 1/2 cup milk; 1/4 cup vegetable oil; 1 teaspoon vanilla extract; 1 large egg

Jump to Recipe

There’s something truly magical about desserts that are both nostalgic and downright delightful, and Pineapple Upside Down Cupcakes deliver just that! Imagine a treat that’s soft, buttery, and crowned with caramelized pineapple and a ruby-red cherry on top—pretty irresistible, right? These cupcakes bring all the joy of the classic cake into a fun, personal-sized portion that’s perfect for sharing (or savoring alone). I still remember my grandma flipping her iconic upside-down cake and marveling at the glossy fruit topping—it was always a showstopper at family gatherings. Now you can bring that same sense of wonder to your own table! These cupcakes are incredibly simple to make, requiring basic pantry staples and just a few spare minutes of prep time. They’re perfect for busy weeknights or special celebrations alike, and kids absolutely love them. If you enjoyed my ever-popular Banana Bread Muffins, you’ll fall for these too; both are fuss-free, crowd-pleasing, and make your home smell amazing. Get ready to enjoy a sweet bite of nostalgia—let’s bake up some pineapple sunshine!

What is Pineapple Upside Down Cupcakes?

Let’s be honest, the name “Pineapple Upside Down Cupcakes” sounds a little topsy-turvy, doesn’t it? Why are desserts sometimes best served upside down? Well, this playful twist on the classic cake gets its name because you build each cupcake starting with the sweet toppings at the bottom of the pan—then flip the whole thing out once it’s baked and golden. It’s fun, fanciful, and a proven way to win hearts. After all, as the old saying goes, the way to a man’s heart is through his stomach! If you’ve ever wondered whether baking could be both whimsical and delicious, these cupcakes are your answer. Try them out and taste the fun for yourself!

Why You’ll Love This

What makes Pineapple Upside Down Cupcakes shine? First, it’s all about that gooey, caramelized fruit topping. Each bite bursts with juicy pineapple, sweet maraschino cherries, and rich brown sugar, making every mouthful an explosion of tropical flavor. Second, making these cupcakes at home is both budget-friendly and incredibly satisfying—no need to splurge at the bakery when you can whip up a dozen from scratch in no time! They’re perfect for sharing with family or bringing to your next potluck. And the best part? The luscious toppings set them apart from your standard vanilla cupcake. If you’re a fan of my Soft Lemon Drizzle Loaf, you’ll appreciate the same bright, vibrant kick here—but with a fun, retro twist! Ready to get baking? Grab your apron and treat yourself to a sunny, sweet experience that’s sure to please everyone.

How to Make

Quick Overview

These Pineapple Upside Down Cupcakes are proof that simple can also mean scrumptious! In under 40 minutes, you can serve up single-serve treats that feature rich, buttery cake topped with juicy fruit and a delicious brown sugar glaze. The preparation is almost foolproof—layer, mix, bake, and flip. No fancy equipment or advanced skills required! Whether you’re baking for a weeknight dessert or a festive get-together, these cupcakes make it easy to impress and indulge.

Ingredients

1/4 cup unsalted butter, melted
1/2 cup brown sugar, packed
12 maraschino cherries, halved
1 cup pineapple chunks (or crushed pineapple, drained)
1 cup all-purpose flour
1/2 cup granulated sugar
1/2 teaspoon baking powder
1/4 teaspoon baking soda
1/4 teaspoon salt
1/2 cup milk
1/4 cup vegetable oil
1 teaspoon vanilla extract
1 large egg

Step-by-Step

Preheat your oven to 350°F (175°C) and lightly grease a 12-cup muffin pan.
Pour the melted butter evenly into the bottom of each muffin cup (about 1 teaspoon per cup). Sprinkle brown sugar on top of the butter in each cup.
Place a halved maraschino cherry in the center of each muffin cup, cut side up. Arrange a few pineapple chunks (or a spoonful of crushed pineapple) around the cherry to cover the bottom.
In a large mixing bowl, whisk together the flour, granulated sugar, baking powder, baking soda, and salt.
In a separate bowl, mix together the milk, vegetable oil, vanilla extract, and egg until smooth.
Pour the wet ingredients into the dry ingredients, stirring just until the batter is combined. Avoid overmixing for the softest cupcakes.
Spoon the batter over the fruit in each muffin cup, filling them about 2/3 full.
Bake for 20-25 minutes, or until the tops are golden and a toothpick inserted into the center comes out clean.
Allow the cupcakes to cool in the pan for about 5 minutes. Then, run a knife around each cupcake, place a baking sheet or wire rack on top of the pan, and carefully invert to release the cupcakes with the pineapple side up.
Serve warm for a gooey, comforting treat—or let them cool completely for an easy-to-pack snack!

What to Serve Pineapple Upside Down Cupcakes With

These sunny little cakes are wonderful on their own, but you can make them truly special with a few simple additions. Pair them with a dollop of softly whipped cream or a scoop of creamy vanilla ice cream for a classic touch. For a tropical-themed dessert spread, add coconut macaroons, a bowl of fresh berries, or tangy lemon bars. These cupcakes are also delightful alongside a cup of hot coffee, iced tea, or a sparkling pineapple cocktail, making them perfect for brunches and afternoon gatherings.

Top Tips for Perfecting

If you don’t have fresh pineapple, canned pineapple works just as well—just be sure to drain it thoroughly to avoid soggy tops.
Substitute coconut oil for vegetable oil and add a sprinkle of shredded coconut to the batter for a fun tropical twist.
Make sure to invert the cupcakes while they’re still warm; allowing them to cool too long in the pan may make them stick.
If maraschino cherries aren’t your thing, try swapping in candied ginger or pecan halves for an unexpected spin.
For a richer flavor, use dark brown sugar instead of light brown sugar.

Storing and Reheating Tips

To keep your Pineapple Upside Down Cupcakes fresh, store them in an airtight container at room temperature for up to two days, or refrigerate for up to four days. If you want to enjoy them warm, simply microwave each cupcake for about 10-15 seconds. These cupcakes also freeze well—wrap individually in plastic wrap and store in a freezer-safe bag for up to two months. Thaw at room temperature and reheat gently in the microwave before serving for the best gooey texture.

FAQs

Can I use pineapple rings instead of chunks?
Absolutely! Just cut the rings to fit into the muffin cups as needed, or use crushed pineapple for easier layering.

Can these cupcakes be made gluten-free?
Yes, you can substitute your favorite gluten-free all-purpose flour blend in the same quantity.

Do I need to line my muffin pan with paper liners?
No, paper liners aren’t recommended for this recipe. The cupcakes need direct contact with the pan to caramelize and flip properly.

What if I don’t have maraschino cherries?
You can skip them or use another colorful fruit such as a raspberry, blueberry, or a small piece of strawberry.

Can I make the batter or assemble these in advance?
It’s best to bake these fresh, as the fruit can release juices and make the batter overly moist if left to sit. You can prepare the fruit and dry ingredients in advance for easy assembly.

Conclusion

Pineapple Upside Down Cupcakes bring a big dose of sunshine and nostalgia to your dessert table, all in a quick and easy package. These whimsical treats layer golden cake with caramelized pineapple and cherries—perfect for sharing, gifting, or keeping all to yourself on a cozy afternoon. With simple ingredients, budget-friendly appeal, and guaranteed smiles, there’s every reason to give this recipe a try today. Don’t forget to check out other crowd-pleasers on the blog for even more fun, family-friendly baking inspiration. Happy baking—may your cupcakes always flip with flair!