Mini Pineapple Upside Down Cakes

These mini pineapple upside-down cakes transform a classic dessert into perfectly portioned treats that balance sweet caramelized pineapple with moist vanilla cake. The individual servings make them ideal for gatherings where guests can enjoy their own personal cake without the fuss of slicing.

I first made these for my daughter's birthday when she requested something different than traditional cupcakes. The look on her face when I flipped them over to reveal the glistening pineapple tops was priceless—now they're our go-to dessert for special occasions.

Ingredients

• Unsalted butter: creates the rich caramel base and ensures you control the salt level
• Brown sugar: adds that deep molasses flavor that makes the caramelized topping irresistible
• Canned pineapple slices: work perfectly for convenience but fresh pineapple can elevate the flavor even more
• Maraschino cherries: provide that classic pop of color and sweet cherry flavor in the center
• All-purpose flour: gives the cake its structure look for unbleached for best results
• Baking powder: ensures the cakes rise properly fresh baking powder is crucial
• Salt: balances the sweetness and enhances all the flavors
• Granulated sugar: sweetens the cake batter without overpowering
• Egg: binds everything together and adds richness
• Milk: moistens the batter room temperature works best
• Vanilla extract: adds warmth and depth to the cake flavor use pure extract for best results

Step-by-Step Instructions

Prepare the Pan:

Preheat your oven to 350°F and thoroughly grease each cup of your muffin tin focusing on the sides. The caramel mixture can stick easily so a generous coating of butter or cooking spray is essential.

Create the Caramel Base:

Melt the butter in a small saucepan over medium heat until it bubbles slightly. Add the brown sugar and stir constantly for about 2 minutes until the mixture becomes smooth and slightly thickened. Immediately divide this mixture among the muffin cups while still hot so it spreads evenly.

Arrange the Fruit:

Place one pineapple slice into each muffin cup pressing it gently into the caramel mixture. The pineapple should fit snugly in the cup. Then place a maraschino cherry in the center hole of each pineapple slice creating that iconic look.

Mix Wet Ingredients:

In a medium bowl beat the egg and granulated sugar with an electric mixer for about 2 minutes until the mixture becomes pale and fluffy. This incorporates air into the batter for a lighter cake. Slowly add the milk and vanilla extract mixing until just combined.

Combine Dry Ingredients:

In a separate bowl whisk together the flour baking powder and salt ensuring even distribution of the leavening agent. This prevents pockets of baking powder that could create bitter spots in your cakes.

Create the Batter:

Gradually add the dry ingredients to the wet mixture folding gently with a spatula. Mix only until no dry streaks remain overmixing will develop gluten and make the cakes tough.

Fill and Bake:

Carefully spoon the batter over each pineapple arrangement filling each cup about threequarters full. The batter will rise during baking. Bake for 20 minutes or until the tops are golden brown and a toothpick inserted comes out clean.

Unmold and Serve:

Allow the cakes to cool in the pan for exactly 5 minutes. This timing is crucial longer and the caramel may harden making removal difficult. Run a knife around each cake and invert onto a serving plate. The warm caramel will drizzle down the sides creating a gorgeous presentation.

Save This

The maraschino cherries are more than just decoration in this recipe. My grandmother always insisted on their inclusion saying they add that perfect hint of brightness that cuts through the sweetness of the caramel. When I tried making these without them once my family immediately noticed something was missing from the flavor profile.

Storage and Freshness

These mini cakes are at their absolute best when served warm shortly after baking when the caramel is still slightly warm and flowing. However if you need to store them place in an airtight container at room temperature for up to two days. To reheat microwave each cake for about 15 seconds or place in a 300°F oven for 5 minutes until warmed through. The texture changes slightly upon storage with the caramel becoming more chewy but the flavor remains delicious.

Creative Variations

While the classic pineapple and cherry combination is timeless this recipe welcomes experimentation. Try using peach slices with a sprinkle of cinnamon for a different flavor profile. Mango chunks work beautifully for a tropical variation. You can even use apple slices tossed with cinnamon for a fall-inspired version. The cake batter also accepts additions like 1/4 teaspoon of almond extract or 1/2 teaspoon of citrus zest to complement your fruit choices.

Serving Suggestions

These mini cakes shine on their own but can be elevated further with thoughtful accompaniments. A small scoop of vanilla ice cream served alongside creates a wonderful temperature contrast with the warm cake. Whipped cream with a hint of rum extract complements the tropical pineapple flavors perfectly. For a more sophisticated presentation drizzle each plate with a small amount of caramel sauce and add a mint leaf for color. These cakes are substantial enough for dessert but light enough to serve with afternoon tea.

Historical Background

The pineapple upside-down cake gained popularity in America during the 1920s after the invention of canned pineapple made tropical fruit widely available to home cooks. Previously pineapples were exotic and expensive treats reserved for special occasions. The concept of cooking fruit in a sweet syrup at the bottom of a pan dates back much further with European tarte tatins and skillet cakes. This mini version maintains all the charm of the original while adapting to modern preferences for individual servings and portion control.

Common Queries

→ Can I use fresh pineapple instead of canned slices?

Absolutely! Just slice fresh pineapple thinly and use it in place of canned. Adjust sweetness if desired.

→ What’s the best way to prevent the cakes from sticking to the muffin tin?

Generously grease the muffin tin before adding ingredients and allow the cakes to cool slightly before loosening with a thin spatula.

→ Can I substitute another fruit for the maraschino cherries?

Yes, try pitted fresh cherries, cranberries, or even a raspberry in each center for a different flavor profile.

→ How should I store leftovers?

Store cooled cakes in an airtight container at room temperature for up to 2 days or refrigerate for longer freshness.

→ Is it possible to freeze these mini cakes?

Yes, after cooling, wrap individually and freeze for up to 2 months. Thaw at room temperature before serving.