Caramelised Crown Pineapple Upside Down Cupcakes

Pineapple Upside Down Cupcakes

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Preparation time:30 Mins

Cooking time:20 Mins

Servings:12 standard cupcakes

Ingredients:

• 6 tablespoons (85g) Unsalted Butter, melted (for topping)
• 1/2 cup (100g) Light Brown Sugar, packed (for topping)
• 12 whole, well drained Maraschino Cherries
• 12 canned Pineapple Rings or equivalent chunks, well drained
• 1 3/4 cups (210g) All-Purpose Flour, sifted
• 3/4 cup (150g) Granulated Sugar
• 2 teaspoons Baking Powder
• 1/2 teaspoon Salt
• 1/2 cup (113g) Unsalted Butter, softened (for batter)
• 2 large Eggs, room temperature
• 1/2 cup (120ml) Whole Milk, room temperature
• 1 teaspoon Vanilla Extract
• 1/2 cup (113g) Unsalted Butter, softened (for frosting)
• 3 cups (360g) Confectioners’ Sugar, sifted
• 2 tablespoons Pineapple Juice (optional)
• 1 teaspoon Dark Rum (optional)

Instructions:

• Preheat oven to 350°F (175°C). Line a standard 12-cup muffin tin with paper liners.
• Melt 6 tbsp of butter. Spoon 1 teaspoon of melted butter into the bottom of each liner. Dust evenly with the brown sugar (about 1 teaspoon per cup).
• Place one pineapple ring neatly over the sugar mixture in each liner. Top the centre of the pineapple with one drained Maraschino cherry.
• In a medium bowl, whisk together the sifted flour, granulated sugar, baking powder, and salt.
• In a separate large bowl, cream the softened butter until pale and fluffy (about 2 minutes).
• Beat in the eggs one at a time, followed by the vanilla extract. Scrape down the sides of the bowl.
• Gradually add the dry ingredients alternately with the milk, beginning and ending with the dry mixture. Mix only until just combined; do not overmix.
• Carefully spoon the batter evenly over the fruit topping in each liner, filling them about 2/3 full.
• Bake for 18 22 minutes, or until a skewer inserted into the cake part (avoiding the sticky base) comes out clean.
• Remove the tin from the oven. Let cool in the tin for exactly 5 minutes.
• Place a wire rack over the tin. In one swift motion, invert the tin onto the rack. If any toppings stick, gently place them back onto the corresponding cupcake immediately.
• Allow the cupcakes to cool fully before frosting. If making buttercream, beat butter until smooth, then gradually add confectioners’ sugar, alternating with pineapple juice/rum, until light and fluffy.
• Pipe or spread frosting onto the cooled cupcake tops.

Nutrition Facts

Calories	367 kcal
Protein	5.0 g
Fat	25.9 g
Carbs	42.9 g
Fiber	0.9 g
Sodium	123 mg

Recipe Info

Category	Dessert
Cuisine	American

Unveiling the Miniature Majesty of Classic Comfort

There’s a special kind of magic that happens when you shrink down a beloved classic. The traditional Pineapple Upside Down Cake is the embodiment of nostalgic baking that perfect marriage of tart fruit, sweet, buttery caramel, and tender sponge.

But let’s be honest: serving that giant, dripping cake can sometimes feel overly formal for a casual gathering or a simple weeknight craving. Enter the Pineapple Upside Down Cupcakes .

We are taking everything wonderful about that iconic dessert and presenting it in perfectly portioned, utterly charming mini desserts . This adaptation transforms a single dessert into twelve individual masterpieces, ensuring every guest gets that ideal balance of sticky topping to light cake ratio.

If you've been searching for irresistible cupcake recipes that offer a tropical twist, your search ends here.

Why Individual Slices Trump the Full Sized Favourite

The appeal of the miniature version goes beyond mere aesthetics; it’s about control, convenience, and maximizing the best elements of the original dish.

A Nostalgic Treat Reimagined for Modern Portions

Why fuss with slicing a sticky, potentially crumbly cake when you can hand out flawlessly formed mini cakes ? These Pineapple Upside Down Cupcakes offer unparalleled ease of serving.

They travel beautifully, are ideal for potlucks, and eliminate the messy cleanup associated with carving up a full sized Pineapple Upside Down Cake . This format allows the complex textures of the dessert to shine without collapsing under their own weight.

The Magic of Caramelised Fruit Meets Fluffy Batter

The heart of this recipe lies in the method: we invert the structure. Instead of layering the fruit on top before baking, we place the caramel and pineapple directly into the base of the liner.

As the light vanilla sponge bakes above, the fruit caramelises beneath it, fusing into a cohesive, intensely flavourful crown once flipped. The resulting texture contrast sticky, molten bottom meeting airy top is what makes this dessert so addictive.

Our Secret to Maximising That Buttery Bottom Layer

The success of any great Pineapple Upside Down Cupcakes Recipe hinges on the base. To achieve that signature glossy, deep caramel, we employ a simple, three part layering process right in the paper liner: melted butter, packed light brown sugar, and perfectly drained pineapple rings, crowned with a vibrant Maraschino cherry.

We spend a dedicated 30 minutes prepping these components before we even think about mixing the cake batter, setting the stage for perfection.

Assembling the Essentials for Perfection

Creating these Pineapple Upside Down Cupcakes From Scratch requires precision, especially in the preparation phase. With a difficulty level rated as Medium mostly due to the careful inverting required proper ingredient staging is paramount.

This recipe yields 12 standard cupcakes and takes about an hour total, excluding cooling time.

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Equipment Required for Crafting Pineapple Upside Down Cupcakes

Before diving into the mixing, ensure your tools are ready. While a basic mixer will suffice, a stand mixer definitely makes the frosting stage easier.

Pantry Staples for the Cake Base

For the moist, tender vanilla sponge that cradles our topping, you will need the standard dry elements: 1 3/4 cups of sifted All-Purpose Flour, 3/4 cup of Granulated Sugar, 2 teaspoons of Baking Powder, and 1/2 teaspoon of Salt.

The wet components are equally important: 1/2 cup (room temperature) of Unsalted Butter, 2 room temperature Large Eggs, 1/2 cup of room temperature Whole Milk, and 1 teaspoon of Vanilla Extract. Using room temperature ingredients ensures everything emufies correctly, resulting in a lighter crumb.

The Crucial Components for the Topping & Caramel

This is where the flavour profile is built. You require 6 tablespoons of Unsalted Butter, melted down, paired with 1/2 cup of packed Light Brown Sugar. For the fruit, we need 12 well drained canned Pineapple Rings (or equivalent chunks) and 12 Maraschino Cherries, also thoroughly drained.

For those who enjoy an extra layer of depth, the optional Pineapple Rum Buttercream calls for another 1/2 cup of softened butter, 3 cups of sifted Confectioners’ Sugar, 2 tablespoons of pineapple juice, and a tiny splash of Dark Rum.

Pro Tips for Selecting the Best Canned or Fresh Pineapple

While fresh pineapple is always a contender, canned rings are often preferred for this specific application because they are consistently sized and already slightly tenderized. If you use canned, the most critical step is draining them completely lay them out on a thick layer of paper towels and blot them dry.

Excess moisture will thin out your caramel base and prevent a crisp set. If opting for fresh, use a ring cutter and pat them aggressively dry.

Step-by-Step Guide to Achieving the Perfect Flip

The method here deviates from standard practice because we are building the dessert upside down. We must prepare the base layer before adding the batter. Begin by preheating your oven to 350° F ( 175° C) and lining a 12-cup muffin tin with paper liners.

Preparing the Signature Caramelised Crown Layer First

In each liner, start by spooning about 1 teaspoon of the melted butter into the bottom. Follow this immediately with an even dusting of light brown sugar roughly 1 teaspoon per cup. Next, carefully place one pineapple ring atop the sugar mixture, ensuring it sits flat against the bottom.

Finally, nestle one drained Maraschino cherry into the centre hole of the pineapple slice. This sets the visual foundation for your Pineapple Upside Down Cupcakes .

Mixing Techniques for Ultra Light Cupcake Sponge

For the batter, use the creaming method. Beat the softened butter until fluffy. Incorporate the eggs one by one, followed by the vanilla. In a separate bowl, whisk together your sifted flour, sugar, baking powder, and salt.

Alternate adding the dry mix and the milk to the creamed mixture, beginning and ending with the dry ingredients. Mix only until the streaks of flour disappear. Over mixing develops gluten, leading to tough cupcakes that won't capture the lightness we seek.

The Critical Moment: Cooling and Inverting Your Baked Goods

Spoon the prepared batter evenly over the fruit layers in each liner, filling them approximately two-thirds full. Bake for 18 to 22 minutes. This is where timing becomes non-negotiable. Remove the tray from the oven, but do not touch the cupcakes for precisely 5 minutes.

This brief cooling period allows the caramel to transition from molten lava to a sticky glaze that just holds its shape.

Troubleshooting Sticky Situation: Ensuring Clean Release

After the 5-minute wait, place a wire cooling rack over the muffin tin and, in one confident, swift movement, invert the entire assembly. If a piece of fruit or cherry adheres to the tin, quickly lift it out with a small offset spatula and gently place it back onto its corresponding cupcake on the cooling rack.

This immediate correction prevents you from losing the signature look of your delicious Pineapple Upside Down Cupcakes . Once inverted, they must cool completely before any frosting is applied.

Elevating Your Pineapple Upside Down Cupcakes Experience

Once cooled, the options for finishing are vast. While these mini desserts are stunning plain, a light swirl of the optional Pineapple Rum Buttercream adds incredible richness and moisture.

For those who enjoy watching baking demonstrations, you’ll often see professional bakers opting for a simple glaze, but the buttercream truly seals the deal on indulgence. If you're documenting your baking journey, this is the stage where you’ll capture the most beautiful food videos desserts footage!

Keeping Freshness Locked In: Storage and Longevity

These Pineapple Upside Down Cupcakes are best eaten the day they are made, as the caramel topping has the most desirable texture when fresh. If you must store them, keep them in an airtight container at room temperature for up to two days.

Avoid refrigeration, as it tends to dry out the cake sponge.

Creative Variations: Nutty Additions and Spiced Twists

To enhance the tropical vibe, try sprinkling toasted, shredded coconut over the brown sugar layer before baking. For a warming counterpoint to the pineapple’s acidity, incorporate 1/2 teaspoon of cinnamon and a tiny pinch of ground cloves into your dry ingredients.

These subtle shifts can turn this simple recipe into an entirely new experience.

Making This Recipe Gluten Free or Vegan Friendly

Adapting this recipe is straightforward. For gluten free baking, substitute the all-purpose flour with a high quality 1:1 gluten free baking blend. For a vegan interpretation, replace the butter with solid coconut oil in both the caramel base and the cake batter, use a plant based milk alternative, and substitute the eggs with commercial egg replacers or flax eggs.

Optimal Cooling Times Before Turning Out Your Treats

Reiterating the importance of timing: the 5-minute cooling window in the pan is non-negotiable before inverting. Any shorter, and the caramel will spill out; any longer, and it will seize in the tin, making removal nearly impossible.

Once inverted onto the rack, allow them to reach ambient temperature about an hour before attempting to frost them.

Serving Suggestions Beyond the Basic Plate

These mini cakes pair beautifully with a chilled glass of Prosecco or a strong, hot cup of black coffee. For a truly decadent presentation, serve them slightly warmed with a very small scoop of high quality vanilla bean ice cream melting delicately over the side.

Enjoy the taste of sunshine, perfectly portioned!