Name: Mini Pineapple Upside-Down Cupcakes Recipe
Prep time: 15 min
Cook time: 25 min
Total time: 40 min
Cuisine: American
Ingredients: 1 can pineapple rings (in juice); 12 maraschino cherries; 12 teaspoons brown sugar; 12 teaspoons unsalted butter (melted); 1 1⁄2 cups all-purpose flour; 1 teaspoon baking powder; 1⁄4 teaspoon salt; 1⁄2 cup unsalted butter (softened); 3⁄4 cup granulated sugar; 2 large eggs; 1⁄2 cup milk; 1 teaspoon vanilla extract

Golden, buttery, and topped with a sweet caramelized pineapple crown, these Mini Pineapple Upside-Down Cupcakes are the kind of treat that brings joy in every bite. They’re like sunshine you can eat, with a gooey brown sugar topping that melts into a fluffy vanilla cupcake base. The classic pineapple upside-down cake gets a miniature makeover that’s perfect for parties, picnics, or a nostalgic dessert anytime you’re craving something sweet and tropical.

Each cupcake is a self-contained moment of pineapple perfection. The brown sugar and butter create a caramel-like glaze that seeps into the pineapple, which bakes into the soft cake below. And the cherry on top? Literally a cherry tucked in the middle of each pineapple ring for that vintage dessert feel with a modern twist.

Why You’ll Love This Mini Pineapple Upside-Down Cupcakes Recipe

These cupcakes are visually stunning and taste even better. You’ll love how simple they are to make using just a handful of pantry staples and a can of pineapple rings. They’re a crowd-pleaser at potlucks and are easy to transport since there’s no need for frosting or decoration beyond what’s baked right in. Plus, who can resist their retro charm?

Whether you’re hosting a summer barbecue or just want a bite of something cheerful on a gray day, these cupcakes deliver sweet satisfaction with minimal fuss. They’re a great way to get kids involved in baking, too, thanks to their hands-on assembly and colorful finish.

What Kind of Pineapple Should I Use?

Canned pineapple rings are the easiest and most classic option for this recipe. They’re the perfect size to fit into a muffin tin and come in sweet juice that adds flavor to the cakes. You can also use pineapple chunks if you prefer a more rustic look or want to skip the cherry centerpiece. If you’re using fresh pineapple, make sure it’s sliced thinly and cut to fit your muffin pan.

Just be sure to pat any pineapple pieces dry before using so the topping doesn’t get too soggy. The right pineapple makes all the difference in texture and balance of sweetness.

Ingredients for the Mini Pineapple Upside-Down Cupcakes

These cupcakes come together with simple ingredients that bring big flavor and gorgeous presentation. Each one plays a role in achieving that buttery caramelized topping and soft vanilla crumb. Here’s what you’ll need to create these sweet little cakes:

Pineapple rings: The star of the show. Use canned pineapple rings in juice for classic flavor and easy handling.
Maraschino cherries: These provide a pop of color and nostalgic sweetness right in the center of each pineapple.
Brown sugar: Adds that essential molasses-rich sweetness to create the gooey, caramel-like topping.
Unsalted butter: Melted butter forms the base of the topping and adds rich flavor throughout the cupcake.
All-purpose flour: Provides structure and body to the cupcake base.
Granulated sugar: Sweetens the cake without overpowering the pineapple.
Baking powder: Lifts the batter so the cupcakes are light and tender.
Salt: Enhances all the flavors and balances the sweetness.
Milk: Adds moisture to the cake and helps bind the ingredients together.
Eggs: Help hold everything together and contribute to the cupcakes’ soft texture.
Vanilla extract: Rounds out the flavor with a warm, sweet aroma.

How To Make the Mini Pineapple Upside-Down Cupcakes

Step 1: Prepare the Muffin Tin

Grease a 12-cup muffin pan well. Place 1 teaspoon of melted butter and 1 teaspoon of brown sugar into each muffin cup. Gently press a pineapple ring (cut in half if needed to fit) into each cavity and place a maraschino cherry in the center.

Step 2: Make the Cupcake Batter

In a medium bowl, whisk together flour, baking powder, and salt. In a separate large bowl, cream together the softened butter and granulated sugar until light and fluffy. Add eggs one at a time, beating well after each. Stir in vanilla extract.

Alternate adding the dry ingredients and milk to the butter mixture, beginning and ending with the dry ingredients. Mix until just combined for a soft, fluffy batter.

Step 3: Assemble and Bake

Spoon the batter evenly over the pineapple slices in the muffin tin, filling each about two-thirds full. Bake in a preheated oven at 350°F (175°C) for 20 to 25 minutes, or until a toothpick inserted into the center comes out clean.

Step 4: Cool and Invert

Let the cupcakes cool in the pan for 5 minutes, then carefully run a knife around the edges and invert onto a wire rack or serving tray. Serve warm or at room temperature and enjoy the glossy pineapple topping on top!

How to Serve and Store These Mini Pineapple Upside-Down Cupcakes

These mini pineapple upside-down cupcakes are best served slightly warm, when the topping is still gooey and the cakes are ultra-soft. They make a charming dessert on their own but also pair beautifully with a scoop of vanilla ice cream or a dollop of whipped cream.

This recipe makes 12 cupcakes, perfect for a small gathering, brunch spread, or dessert tray. If you’re serving them at a party, you can make them ahead of time and reheat slightly in the microwave for about 10 seconds to bring back that fresh-from-the-oven warmth.

To store, allow the cupcakes to cool completely and place them in an airtight container. Keep them at room temperature for up to 2 days or refrigerate for up to 5 days. If refrigerating, let them come to room temperature or warm slightly before serving for the best flavor and texture.

You can also freeze them! Wrap each cupcake individually in plastic wrap, then store in a freezer bag for up to 2 months. Thaw overnight in the refrigerator or reheat gently in the microwave before enjoying.

What to Serve With Mini Pineapple Upside-Down Cupcakes?

A scoop of vanilla bean ice cream

The rich creaminess of vanilla bean ice cream complements the caramelized pineapple topping like a dream.

Fresh coconut whipped cream

A tropical twist that adds lightness and enhances the island-inspired flavor profile.

Spiced rum glaze drizzle

Drizzle a bit of spiced rum glaze over the cupcakes for an adult-friendly finish that deepens the flavors.

Iced coffee or cold brew

The slightly bitter notes of coffee balance the sweetness of the cupcakes perfectly.

Grilled pineapple spears

Double down on pineapple by serving with warm, grilled pineapple slices dusted with cinnamon.

Macadamia nuts or toasted pecans

A small bowl of buttery nuts on the side adds crunch and richness to contrast the soft cupcakes.

Tangy fruit salad

Balance the sweet with a medley of fresh berries, kiwi, and citrus for a refreshing accompaniment.

Mini tropical cocktails

Serve these cupcakes with small glasses of pina colada or a pineapple mojito to keep the tropical vibes going.

Want More Cupcake Ideas with a Twist?

If you loved these mini pineapple upside-down cupcakes, here are more cupcake creations worth exploring:

Irresistible Blueberry Lime Cheesecake Cupcakes with a creamy tang and zesty kick.
Churro Cheesecake Donut Cookies for a cinnamon-sugar hybrid that feels like fair food in cookie form.
Lemon Truffles Recipe when you want a pop of citrusy brightness in bite-size dessert form.
Peanut Butter S’mores Sandwich Cookies if you’re craving campfire flavors in a chewy, nutty package.
Ooey Gooey Butter Cake for a melt-in-your-mouth, buttery indulgence.

Save This Recipe For Later

📌 Save this recipe to your Pinterest dessert board so you can come back to it any time.

And let me know in the comments how yours turned out. Did you use fresh pineapple or stick with canned? Any fun twists like coconut flakes or rum added to the mix?

I love hearing how others make these recipes their own. Questions are welcome too — let’s help each other bake smarter.

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Conclusion

These mini pineapple upside-down cupcakes are a delightful combination of vintage charm and modern convenience. With their gooey tops, tender cake, and sunny flavor, they deserve a place in your regular dessert rotation. Whether you’re baking for guests or indulging solo, these cupcakes bring tropical joy to every table. They’re easy to love, easier to make, and unforgettable after just one bite.