Name: Pineapple Upside-Down Cupcakes
Prep time: 20 min
Cook time: 20 min
Total time: 40 min
Ingredients: 1/2 cup melted butter (for the topping); 1 1/2 cups brown sugar (for the topping); 24 maraschino cherries; 1 (20 oz) can crushed pineapple (well-drained); 1 (18.25 oz) package pineapple cake mix (such as Duncan Hines® Pineapple Supreme); 1 1/3 cups pineapple juice (reserved from the crushed pineapple); 3 large eggs; 1/3 cup vegetable oil; 1 tbsp confectioners' sugar (optional, for dusting)

So here’s the deal—I had a craving for pineapple upside-down cake but didn’t want to mess with a big pan or slicing pieces. Ended up trying it in cupcake form and honestly… it just works. You still get the buttery brown sugar, the pineapple, the cherry in the middle—but it’s all baked into these little individual cakes. They’re a bit messy, in the best way, and somehow taste even better the next day. I made a batch for a family get-together and they were gone before I even sat down.

Why You’ll Absolutely Love These (Yes, Even if You’re Not a Pineapple Fan)

Alright, let’s talk about why these little guys are so irresistible. I could gush all day, but here’s the short list:

Tropical Vacation in a Bite – The pineapple, brown sugar, and maraschino cherry combo is like a tiki drink dressed up for dessert.
Built-in Portion Control – Which means you can have two without feeling like you’re going overboard. (I won’t tell if you grab three.)
Weeknight-Easy – Thanks to cake mix and pantry staples, you’ll go from zero to cupcake hero in under an hour.
Dress Them Up or Keep It Simple – A dusting of sugar, a swoosh of whipped cream, maybe even some toasted coconut if you’re feelin’ fancy.

Let me walk you through the how-to—and toss in some of my favorite variations and shortcuts, because who doesn’t love a good shortcut?

Key Ingredients:

Here’s what’s going into the mix, and a few ways to make it work for different tastes and dietary needs.

Cake Mix – Pineapple cake mix is ideal, but yellow or vanilla works just fine.
Maraschino Cherries – Sweet, juicy. Prefer more pineapple? Swap in a chunk of the fruit instead.
Crushed Pineapple – Be sure to drain it well, or your cupcakes might get a little too soggy on the bottom.
Brown Sugar & Butter – That’s the magic combo for the sticky-sweet base. Want to go dairy-free? Coconut oil or margarine gets the job done—and adds a subtle tropical flair.
Eggs, Oil, and Pineapple Juice – These bring the cake mix to life. If your can of pineapple doesn’t give you quite enough juice, a little water or store-bought juice works just fine.

Now that we’ve got our lineup, let’s get to baking.

For the full ingredient amounts and instructions, see the recipe card below

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Step-by-Step Instructions

Step 1: Preheat That Oven

Set it to 350°F (175°C). While it’s warming up, spray your muffin pan (24 cups, standard size) with cooking spray. This is key unless you like scraping cake out with a spoon.

Step 2: Build the Topping

Drop 1 teaspoon of melted butter into each cup.
Sprinkle in 1 tablespoon of brown sugar.
Add one maraschino cherry right in the middle.
Then spoon in a generous tablespoon of crushed pineapple. Press it down a bit to even things out.

Step 3: Make the Cake Batter

In a big mixing bowl, combine:

1 box of pineapple cake mix
Reserved juice from the crushed pineapple
3 eggs
1/3 cup vegetable oil

Mix it up—start slow for 30 seconds, then beat on medium for about 2 minutes until it’s smooth.

Step 4: Fill ’Em Up

Pour the batter over the pineapple mixture in each cup. Fill them about 2/3 of the way up so they have room to rise without making a mess.

Step 5: Bake

Bake for about 20 minutes, or until a toothpick poked into the middle comes out clean. Don’t overdo it—these can go from moist to dry if you blink too long.

Step 6: The Flip

Let the cupcakes cool for 5 minutes. Then run a knife around the edges and carefully flip the pan over onto a lined baking sheet. If a little topping sticks to the pan, no worries—just spoon it back on top.

Step 7: Sugar Dusting (Optional but Pretty)

A light dusting of confectioners’ sugar adds just the right amount of fancy flair. And it’s tasty, too.

Serving Suggestions:

These Pineapple Upside-Down Cupcakes should really be eaten warm but are delicious at room temperature as well. There are many ways to serve them; here are some ideas:

With Ice Cream: Serve each cupcake with a scoop of vanilla ice cream, for a classic pairing.The cool, creamy ice cream contrasts beautifully with the warm, caramelized pineapple.

Whipped Cream: For a fluffy, light topping, put a dollop of whipped cream on every cupcake.

Toasted Coconut: For a crunchy, tropical element, top the cupcakes with a scatter of toasted coconut flakes.

Storage and Reheating Tips:

To store: Place any leftover cupcakes in an airtight container and place in refrigerator for up to 3 days. For a cold dish or warmed as can be the case.

To reheat: Microwave for 15-20 seconds or place in a 350°F (175 °C) oven for 5 minutes to warm.

They freeze well: These cupcakes freeze great! Wrap each cupcake tightly in plastic wrap, place in a freezer-safe container, and freeze for up to 3 months. Defrost overnight in the refrigerator before serving.

Recipe Variations:

Pineapple and Coconut Cupcakes: Mix in 1/2 cup shredded coconut to the cake batter for another dose of tropical flavor.

Rum-Spiked Topping: For an adult rendition, whisk a tablespoon of dark rum into the melted butter and brown sugar mixture for a Pina Colada-inspired pudding.

Mini Pineapple Upside-Down Cupcakes: These bite-sized versions of a classic cake call for a mini muffin tin. Simply lower the baking time to around 12 to 15 minutes.

Conclusion:

I started making these pineapple upside-down cupcakes on a whim, and now they’re kind of a thing around here. Same cozy flavor as the old-school cake, but in little single servings that are easy to grab and go. The tops get all gooey and buttery, just how they should.

They’re great for pretty much anything—barbecues, birthdays, or just when you feel like baking something sweet. They never last long at our house.