Mini Pineapple Upside Down Cakes Recipe

These Mini Pineapple Upside Down Cakes deliver all the nostalgic flavor of the classic dessert in perfect individual portions! With their caramelized brown sugar topping, sweet pineapple rings, and tender buttery cake, these charming treats balance sweet and tangy flavors in every bite. Ready in under an hour, they’re impressive enough for special occasions but simple enough for weekend baking projects.

Why You’ll Love This Recipe

Perfect Portion Control: Unlike traditional pineapple upside down cake, these mini versions give everyone their own perfect serving with that ideal ratio of caramelized topping to cake.
Impressive Presentation: These little cakes look absolutely stunning when turned out, with their gleaming caramel tops, perfect pineapple rings, and bright cherry centers. They’re guaranteed to make guests think you spent hours in the kitchen!
Better Caramelization: The individual portions mean more of that delicious caramelized edge per serving. Trust me, that’s where all the magic happens!
Make-Ahead Friendly: These mini cakes actually taste even better the next day when the flavors have had time to meld together. Perfect for planning ahead for parties or gatherings.

Ingredients You’ll Need

Butter: Creates a rich, moist texture in the cake and helps form that irresistible caramel topping. Make sure it’s at room temperature for the cake batter.
Brown Sugar: Provides that signature caramel flavor and creates the glossy, sticky topping that makes these cakes so special. I find light brown sugar works perfectly, but dark would give a deeper molasses flavor.
Pineapple Rings: The star of the show! They caramelize beautifully while baking and provide that perfect balance of sweet and tangy. Pat them dry before using to prevent excess moisture.
Maraschino Cherries: Not just pretty decoration—they add a pop of color and that classic sweet cherry flavor. Make sure to get ones without stems for easier placement.
Cake Flour: Results in a lighter, more tender crumb than all-purpose flour. The cake stays soft while still being sturdy enough to hold up to the topping.
Baking Powder: Provides the perfect rise without making the cakes too fluffy or crumbly.
Salt: Enhances all the flavors and balances the sweetness. Don’t skip it!
Granulated Sugar: Sweetens the cake and helps create a tender texture.
Eggs: Provide structure and richness to the cake. Room temperature eggs incorporate much better into the batter.
Crushed Pineapple: Adds moisture and intensifies the pineapple flavor throughout the cake. Be sure to drain it well.
Vanilla Extract: Rounds out the flavors with its warm, aromatic notes.
Buttermilk: Creates a tender crumb and adds a subtle tang that complements the sweet pineapple perfectly.

Note: You’ll find the complete list of ingredients, along with their exact measurements, in the printable recipe card at the bottom of this post.

Variations

Want to switch things up? Here are some delicious twists on this classic:

Tropical Twist: Add 1/2 cup shredded coconut to the batter and replace vanilla extract with coconut extract for a piña colada inspired treat.
Boozy Version: Add 2 tablespoons of rum to the caramel mixture for a sophisticated rum-infused caramel topping.
Mixed Fruit: Swap some of the pineapple rings for peach or mango slices for a unique fruit medley version.
Spiced Cake: Add 1 teaspoon of cinnamon and 1/4 teaspoon of nutmeg to the cake batter for a warm, spiced variation that’s perfect for fall.
Citrus Infusion: Add 1 tablespoon of orange or lemon zest to the batter for a bright, citrusy note that pairs beautifully with the pineapple.

How to Make Mini Pineapple Upside Down Cakes

Step 1: Prepare the Topping

Preheat your oven to 350°F and spray a jumbo muffin tin generously with baking spray. In a small saucepan, melt the butter and brown sugar together, whisking constantly until smooth and combined, about 3-5 minutes. Divide this caramel mixture evenly among the 12 muffin cups, creating a thin layer on the bottom of each.

Step 2: Add Fruit

Place a pineapple ring on top of the caramel in each muffin cup, gently pressing down. Add a maraschino cherry in the center of each pineapple ring. The presentation will be stunning when flipped!

Step 3: Prepare the Cake Batter

In a large bowl, whisk together the cake flour, baking powder, and salt. In your stand mixer with the paddle attachment, cream the softened butter with both sugars until light and fluffy, about 3 minutes. Add eggs one at a time, ensuring each is fully incorporated before adding the next.

Step 4: Finish the Batter

Mix in the crushed pineapple and vanilla extract. Then, alternately add the dry ingredients and buttermilk to the batter, starting and ending with the flour mixture. Mix just until combined, being careful not to overmix.

Step 5: Bake to Perfection

Divide the batter evenly among the prepared muffin cups, filling each about 3/4 full. Bake for 20-25 minutes until the cakes are golden brown and a toothpick inserted in the center comes out clean.

Step 6: The Big Reveal

Let the cakes cool in the pan for exactly 10 minutes—this is crucial! Place a sheet tray over the muffin tin and carefully flip everything over. Wait 5 more minutes before lifting the tin off the cakes, allowing the caramel to set slightly and release from the pan.

Pro Tips for Making the Recipe

Room Temperature Ingredients: Make sure your eggs and buttermilk are at room temperature for the smoothest, most evenly mixed batter.
Don’t Rush the Flip: That 10-minute cooling period is non-negotiable! Too soon and the cakes might fall apart; too late and the caramel could harden and stick to the pan.
Proper Pan Preparation: Be generous with the baking spray in the muffin cups—these cakes are sticky by nature and need help releasing cleanly.
Even Batter Distribution: Use a cookie scoop or measuring cup to ensure each cake gets the same amount of batter for even baking.
Pineapple Prep: Pat the pineapple rings dry with paper towels before placing them in the pan. Excess moisture can make the caramel sauce too thin.
Caramel Watchfulness: Keep a close eye on the butter and sugar mixture as it melts. It can go from perfect to burned in seconds.

How to Serve

These mini cakes shine all on their own, but here are some delightful serving suggestions:

Simple Elegance

Serve slightly warm with a dusting of powdered sugar for a simple yet elegant presentation.

Dessert Upgrade

Add a small scoop of vanilla ice cream on top of each warm cake and watch it melt into the caramel sauce—absolutely heavenly!

Brunch Favorite

Believe it or not, these make a wonderful brunch item paired with a cup of hot coffee or a mimosa for special occasions.

Dessert Board

Create a dessert board with these mini cakes as the centerpiece, surrounded by fresh fruit, whipped cream, and bite-sized chocolates.

Make Ahead and Storage

Storing Leftovers

These cakes stay moist for days! Store them in an airtight container at room temperature for up to 2 days or in the refrigerator for up to 5 days. The flavor actually improves after the first day as the caramel continues to seep into the cake.

Freezing

Yes, you can freeze these little beauties! Wrap each cake individually in plastic wrap and then aluminum foil, or place in freezer-safe containers. They’ll keep for up to 3 months.

Reheating

For the best texture and flavor, thaw frozen cakes in the refrigerator overnight. Reheat individual cakes in the microwave for 15-20 seconds or in a 300°F oven for about 5-7 minutes until just warm. This reactivates the gooey caramel topping and makes them taste freshly baked!

FAQs

Can I use a regular muffin tin instead of a jumbo one?

Absolutely! You’ll just need to adjust the baking time down to about 15-18 minutes. The recipe will likely make more than 12 in a standard muffin tin, so prepare accordingly. The pineapple rings might need to be cut down to fit, or you can use crushed pineapple for the topping instead.

Why did my caramel harden or crystallize?

This usually happens when the sugar mixture is heated too quickly or not whisked constantly. Keep the heat medium-low and whisk continuously until the sugar is completely dissolved. If you see any sugar crystals forming on the sides of the pan, brush them down with a wet pastry brush.

Can I make these without the cherries?

Certainly! The cherries are traditional but not essential. You can leave them out entirely or replace them with a pecan half, a blueberry, or even a small piece of another fruit that pairs well with pineapple.

What can I substitute for buttermilk?

If you don’t have buttermilk on hand, make your own by adding 2 teaspoons of lemon juice or white vinegar to 3/4 cup of regular milk. Let it sit for 5 minutes before using. Alternatively, plain yogurt thinned with a little milk works well too.

Final Thoughts

These Mini Pineapple Upside Down Cakes bring all the nostalgic flavor of grandma’s classic dessert in perfect individual portions. The combination of buttery caramel, sweet pineapple, and tender cake creates an irresistible treat that’s both impressive and comforting. Whether for a dinner party, holiday gathering, or simply because you deserve something special, these little cakes are sure to bring smiles all around. So fire up that oven, break out the jumbo muffin tin, and prepare to fall in love with this perfectly portioned classic!