Mini Pineapple Upside Down Cakes are soft, fluffy individual cakes topped with juicy pineapple, sweet maraschino cherries, and an irresistible buttery, caramel-like crust!

If you love the sweet combination of pineapple and cherry, you’ll want to try my Pina Colada Bites and Pina Colada Dip that are packed with irresistible pineapple and cherry treats, too!

Why you’ll love this recipe:

Mini Pineapple Upside Down Cakes transform a simple boxed cake mix into adorable individual-sized desserts with juicy crushed pineapple, sweet maraschino cherries, and that irresistible caramel-like crust everyone loves about the classic.

If you love pineapple upside down cake, you are going to love this mini version. They have all of the nostalgic flavors of the classic dessert, but they’re baked into individual portions that are so much easier to serve and even more fun to eat.

And the best part? You start with a boxed cake mix, so these couldn’t be much easier to make!

There is something so good about the combination of warm pineapple, buttery brown sugar, cherries, and fluffy yellow cake. Every bite is sweet, fruity, buttery, and incredibly comforting.

The pineapple adds a bright, juicy flavor that cuts through the sweetness of the cake, while the brown sugar and butter create that delicious caramel-like topping as everything bakes together. The maraschino cherry in the center adds a pop of sweetness and gives these cakes that unmistakable pineapple upside down cake look.

Making them mini just makes the whole dessert feel a little more special. Instead of cutting slices from one large cake, everyone gets their own individual pineapple upside down cake.

They’re also much easier to serve at parties, potlucks, showers, holidays, or family gatherings. Just flip them out of the pan and they’re ready to go!

Ingredients you’ll need:

Brown sugar
Butter- melted
Marashino cherries- stems removed
Pineapple tidbits- juice reserved
Yellow cake mix
Vegetable oil
Eggs

These little cakes taste just like the classic pineapple upside down cake you know and love, but in a perfectly portioned size.

The cake itself is soft, fluffy, and buttery with the sweet flavor of yellow cake. On top, the crushed pineapple becomes tender and juicy while the butter and brown sugar melt together to create a rich, caramel-like crust.

Then there’s the maraschino cherry. It’s sweet, slightly fruity, and adds just the right finishing touch!

The combination is almost like a pineapple cake crossed with a buttery caramel dessert. They’re sweet without being complicated, and the contrast between the fluffy cake and sticky pineapple topping makes every bite so good.

While there is absolutely nothing wrong with a classic pineapple upside down cake, these individual cakes are just so convenient!

You don’t have to worry about cutting perfect slices or figuring out how to serve a sticky cake at a party. Each person can simply grab their own mini cake.

They’re also a great option when you want a dessert that looks impressive without requiring a lot of effort. No one needs to know that the recipe started with a boxed cake mix!

I also love that they’re small enough to enjoy without committing to a huge slice of cake. Although, fair warning, it’s pretty easy to go back for another one!

How to make the best Mini Pineapple Upside Down Cakes:

Preheat your oven to 350 degrees F and grease two 12-count standard sized muffin tins with non-stick cooking spray.
In a medium sized bowl, combine the brown sugar and melted butter, then distribute the mixture evenly between 18 of the greased muffin cups, about 1 tablespoon per cup.
Place 1 maraschino cherry in the middle of each muffin cup, then open your can of pineapple tidbits, reserve the juice, and spoon 1 to 1 ½ tablespoons of the pineapple between all 18 muffin cups. Set aside.
In a large mixing bowl, combine the cake mix, 1 cup of reserved pineapple juice, vegetable oil, and eggs, mix until smooth, then divide the batter evenly among each muffin cup
Bake for 20 to 25 minutes or until a toothpick inserted into the center of the cakes comes out clean.
Remove from the oven and allow to cool in the pan for 5 to 10 minutes. Slide a knife around the outside of each cake (to loosen them from the pan), then place a wire rack on top of the muffin pan.
Carefully flip the wire rack over with the muffin pan on top. Gently remove the muffin pan to release the cakes. If some of the topping happens to stick to the pan, just spoon it out and gently place it back on top of the cakes.
Allow to cool, then serve and enjoy! These are delicious served warm with a scoop of vanilla ice cream or freshly whipped cream.

I love recipes like this because they prove you don’t need a complicated recipe or a long ingredient list to make an incredible dessert.

A simple boxed cake mix becomes something completely different when you layer it with buttery brown sugar, crushed pineapple, and maraschino cherries. Once those ingredients bake together, you end up with these irresistible little cakes that taste like you spent much more time making them than you actually did.

If you’re looking for an easy pineapple upside down cake recipe, these mini cakes are such a fun one to try. They’re nostalgic, simple, and perfect for sharing—or keeping a few for yourself.

Whether you’re making them for a party or just want an easy dessert for the weekend, these Mini Pineapple Upside Down Cakes are guaranteed to disappear quickly. They’re soft, buttery, fruity, caramelized, and completely delicious!

My top tips:

GREASE YOUR MUFFIN TINS: If you’re worried about sticking, give the muffin pan a generous coating of nonstick spray before adding the butter and brown sugar mixture. You can also gently run a butter knife around the edges of each cake before inverting the pan.
PINEAPPLE JUICE: Be sure to drain the crushed pineapple well before adding it to the muffin cups. You want plenty of pineapple flavor, but too much extra liquid can make the cakes overly wet.
BAKING: Just like most cakes, you can use a toothpick to insert in the center of the cupcake. Try to stay in the middle and not go all the way down into the brown sugar. If the toothpick comes out mostly clean and not wet, they’re done!
COOLING: Don’t let the cakes cool in the pan too long. If you do, the topping is more than likely going to stick to the pan. I only let mine cool for 5 to 10 minutes before flipping them. If a little bit of the topping happens to stick, you can just spoon it right back on top of the cakes and no one will ever know!
INVERTING: You’ll also want to flip the cakes while they’re still warm. If they cool completely in the pan, the buttery brown sugar topping can firm up and make them harder to remove. Don’t skip the cooling time, though. Let them sit for a few minutes after coming out of the oven so the cakes can settle slightly before you turn them out.
STORING: Cakes may be stored in an airtight container at room temperature for up to 2 days or in the fridge for up to 4 days. These cakes will freeze well for 2 to 3 months. Thaw overnight in the fridge and bring to room temperature before serving.
MAKE AHEAD: These are a great dessert to make ahead of time. Once cooled, store the mini cakes in an airtight container in the refrigerator until you’re ready to serve them. You can enjoy them chilled, let them come to room temperature, or warm them slightly before serving. If you’re serving them with ice cream, I definitely recommend warming them up first.
SERVING: These mini pineapple upside down cakes are delicious all on their own, especially while they’re still slightly warm.If you want to make them extra indulgent, serve them with a scoop of vanilla ice cream. The cold, creamy ice cream melting into the warm pineapple and caramel-like topping is seriously hard to beat.

Looking for more mini versions of classic desserts? Check these out!

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