Sweet Pineapple Upside Down Cupcakes: A Tropical Treat!

Pineapple Upside Down Cupcakes are truly a delightful twist on a cherished classic, offering all the joy of the original cake in a perfectly portioned package. I remember the first time I encountered the iconic pineapple upside-down cake – its vibrant, caramelized pineapple rings and cherries beckoned, promising a taste of tropical sunshine. This beloved dessert, which truly soared in popularity in the United States during the early 20th century, thanks in part to the convenience of canned pineapple, has always held a special place in many hearts. Its unique preparation, where the fruit forms the bottom of the pan before the batter is added, creates that signature sweet, sticky, and slightly tangy topping once inverted.

Why We Love This Modern Classic

Now, imagine all that deliciousness, but miniaturized for individual enjoyment and effortless serving! That’s precisely what you’ll find with these amazing Pineapple Upside Down Cupcakes. People simply adore this version for its unbeatable combination of moist, tender cake, the luscious caramelized pineapple, and that irresistible hint of buttery brown sugar. They offer a perfect balance of sweet and tart, and the individual servings make them ideal for parties, lunchboxes, or simply a convenient treat at home. Get ready to bake a batch of happiness that brings a nostalgic smile with every single bite!

Ingredients:

• For the Caramel Topping:

• 6 tablespoons (85g) unsalted butter, melted
• ½ cup (100g) packed light brown sugar
• 12 slices canned pineapple rings (about 20 oz can), well-drained
• 12 maraschino cherries, well-drained and patted dry with paper towels

• For the Pineapple Upside Down Cupcakes Batter:

• 1 ½ cups (190g) all-purpose flour
• 1 ½ teaspoons baking powder
• ½ teaspoon salt
• ½ cup (113g) unsalted butter, softened to room temperature
• 1 cup (200g) granulated sugar
• 2 large eggs, room temperature
• 1 teaspoon vanilla extract
• ½ cup (120ml) milk (whole or 2% works best), room temperature

• Optional Garnish:

• Whipped cream or a dollop of vanilla ice cream
• Fresh mint leaves

Prepping for Pineapple Upside Down Cupcakes: The Caramel & Fruit Layer

1. Preheat your oven and prepare your muffin pan: Begin by preheating your oven to 350°F (175°C). This ensures the oven is at the correct temperature when your cupcakes are ready to go in, which is vital for proper rising. Line a 12-cup standard muffin tin with paper liners. While some recipes suggest not using liners for upside-down cakes, for these Pineapple Upside Down Cupcakes, I find that liners actually help immensely with the inversion process and prevent the sticky caramel from adhering too much to the pan, making for easier cleanup and perfect individual servings.
2. Prepare the caramel base in each liner: In a small, microwave-safe bowl or saucepan, melt the 6 tablespoons of unsalted butter until fully liquid. This usually takes about 30-45 seconds in the microwave. Once melted, carefully pour an equal amount of the melted butter into the bottom of each of the 12 prepared muffin liners. You’re aiming for a thin, even layer in each cup.
3. Add the brown sugar: Next, sprinkle approximately 1 tablespoon (or a generous half tablespoon if you prefer less sweetness) of packed light brown sugar over the melted butter in each muffin liner. This combination of butter and brown sugar will melt and caramelize beautifully during baking, creating the signature gooey, golden topping for our Pineapple Upside Down Cupcakes.
4. Arrange the pineapple: Take your well-drained canned pineapple rings. Since standard pineapple rings are often too large to fit perfectly into a muffin cup, you’ll likely need to cut them. I usually cut each ring into quarters or halves, depending on the size of the ring and how much pineapple I want in each cupcake. Arrange one piece (or two smaller pieces if quarters) of pineapple artfully on top of the brown sugar and butter mixture in each liner. Try to make sure the pineapple lays relatively flat against the bottom of the liner.
5. Place the maraschino cherries: Finally, take your well-drained and patted dry maraschino cherries. Place one cherry (or half if you prefer) in the center of each pineapple arrangement. The vibrant red of the cherry will provide a lovely color contrast against the golden pineapple, making your finished Pineapple Upside Down Cupcakes visually stunning. Patting them dry helps prevent excess moisture from interfering with the caramel.
6. Set aside: Carefully set the prepared muffin tin aside while you prepare the cupcake batter. Try not to jostle it too much to keep the fruit and caramel layer intact.

Crafting the Perfect Cupcake Batter

7. Combine dry ingredients: In a medium bowl, whisk together the all-purpose flour, baking powder, and salt. Whisk these dry ingredients together thoroughly for about 30 seconds. This step is crucial for ensuring that the leavening agent and salt are evenly distributed throughout the flour, preventing pockets of unmixed ingredients and guaranteeing a consistent rise and flavor in your Pineapple Upside Down Cupcakes. Set this bowl aside for a moment.
8. Cream butter and sugar: In a large mixing bowl, using an electric mixer (either a stand mixer with the paddle attachment or a handheld mixer), beat the softened unsalted butter on medium speed for about 1 minute until it’s light and creamy. Then, gradually add the granulated sugar, continuing to beat on medium-high speed for another 2-3 minutes. You want the mixture to become pale yellow, light, and fluffy. This process incorporates air into the butter, which contributes significantly to the light and tender texture of the finished cupcakes.
9. Add eggs one at a time: Crack one large egg into the creamed butter and sugar mixture. Beat on medium speed until just combined, scraping down the sides of the bowl as needed to ensure everything is incorporated. Then, add the second egg and repeat the process. Adding eggs one at a time allows for better emulsification and prevents the mixture from curdling. Continue to beat until the mixture is homogenous and slightly increased in volume.
10. Stir in vanilla extract: Add the vanilla extract to the mixture and beat for another 15-20 seconds until fully incorporated. Vanilla adds a wonderful aromatic depth that complements the pineapple beautifully.
11. Alternate dry and wet ingredients: Now, it’s time to incorporate the dry ingredients and the milk. With the mixer on low speed, add about one-third of the dry ingredient mixture to the wet ingredients. Mix until just combined. Then, pour in half of the milk and mix until just combined. Repeat this process, adding another third of the dry ingredients, then the remaining milk, and finally the last third of the dry ingredients. The key here is to mix only until just combined after each addition. Overmixing the batter can develop the gluten in the flour too much, resulting in tough, dry cupcakes.
12. Perform a final gentle fold: Once all ingredients are added, remove the bowl from the mixer and use a rubber spatula to give the batter a few gentle folds. Scrape down the sides and bottom of the bowl to ensure there are no pockets of unmixed flour or butter. The batter should be smooth, thick, and consistent.

Baking Your Delightful Pineapple Upside Down Cupcakes

13. Fill the cupcake liners: Carefully spoon the cupcake batter into the prepared muffin liners, dividing it evenly among the 12 cups. Fill each liner approximately two-thirds full. Be mindful not to disturb the fruit and caramel layer underneath too much. A cookie scoop can be very helpful here for even portioning.
14. Bake the cupcakes: Transfer the muffin tin to your preheated 350°F (175°C) oven. Bake for approximately 20-25 minutes. Baking times can vary slightly depending on your oven, so keep an eye on them.
15. Check for doneness: To check if your Pineapple Upside Down Cupcakes are ready, insert a wooden skewer or a toothpick into the center of one of the cupcakes (avoiding the pineapple layer at the very bottom). If it comes out clean or with only a few moist crumbs attached, they are done. If it comes out with wet batter, bake for a few more minutes and retest. The tops of the cupcakes should be lightly golden brown and spring back when gently pressed.

Cooling and Presentation for Your Pineapple Upside Down Cupcakes

16. Cool briefly in the pan: Once baked, remove the muffin tin from the oven. Let the Pineapple Upside Down Cupcakes cool in the pan for just 5-7 minutes. This short cooling period allows the caramel to set slightly but not harden completely, making the inversion process much easier. It’s crucial not to let them cool too long in the pan, or the caramel might stick.
17. Invert the cupcakes: This is the exciting part! Place a large wire cooling rack directly over the top of the muffin tin. With oven mitts protecting your hands, carefully but quickly invert the entire muffin tin onto the wire rack. Let it sit upside down for about 1-2 minutes. This allows gravity to help release the caramel and fruit topping onto the top of each cupcake.
18. Gently remove the pan and liners: After the short inversion period, gently lift the muffin tin away. The cupcakes, with their beautiful caramel and pineapple topping, should now be sitting right side up on the cooling rack. Carefully peel off the paper liners from each cupcake. The caramel should have adhered nicely to the cake. If any caramel or fruit sticks to the liner, you can gently scrape it off with a small spoon and place it back on the cupcake.
19. Cool completely: Allow the Pineapple Upside Down Cupcakes to cool completely on the wire rack before serving. This is important for the structure of the cake and allows the flavors to meld. The caramel will also firm up slightly as it cools.
20. Serve and enjoy: These delightful Pineapple Upside Down Cupcakes are best enjoyed the same day they are baked for optimal freshness and texture. If desired, you can serve them warm with a dollop of whipped cream or a scoop of vanilla ice cream. A small fresh mint leaf can add a lovely touch of color and aroma.
21. Storage: Store any leftover Pineapple Upside Down Cupcakes in an airtight container at room temperature for up to 2 days, or in the refrigerator for up to 3-4 days. While they are still delicious, the caramel may soften slightly over time.

Conclusion:

And so, we arrive at the sweet, satisfying culmination of our culinary journey! I genuinely hope you’ve enjoyed delving into the details of this truly delightful recipe. From the moment you caramelize that beautiful pineapple ring to the magic of the flip, these cupcakes are designed to bring a little sunshine to your kitchen and a huge smile to your face. They’re more than just a dessert; they’re a miniature celebration, a perfect blend of tropical sweetness and comforting cake. The tender, moist crumb infused with that signature pineapple flavor, crowned with the glistening, caramelized fruit and a vibrant cherry, creates an irresistible treat that is simply a must-try. I promise you, the aroma alone as they bake will transport you to a sunny paradise, and the taste? Pure bliss! It’s this unique combination of visual appeal, ease of preparation, and utterly delicious flavor that makes these particular Pineapple Upside Down Cupcakes stand out as a recipe you’ll want to revisit again and again.

Making Them Your Own: Serving Suggestions & Creative Variations

Once your beautiful cupcakes have cooled slightly, the real fun begins with presentation! While they are absolutely divine enjoyed warm, just as they are, a little extra flourish can elevate them even further. Imagine serving them alongside a generous dollop of freshly whipped cream, perhaps infused with a hint of coconut extract for an extra tropical kick. Or, for a truly decadent experience, a small scoop of high-quality vanilla bean ice cream melting gently next to a warm cupcake is a match made in heaven. A light dusting of toasted coconut flakes adds both texture and another layer of tropical flavor, while a fresh mint sprig can provide a lovely pop of color and freshness. Don’t be afraid to experiment! These cupcakes are incredibly versatile.

Thinking beyond the basic serving, consider how you might personalize the recipe itself. Feeling adventurous? Try swapping out the pineapple for other fruits like thinly sliced peaches, a ring of crisp apple, or even a mix of berries (though these might be better nestled directly into the batter rather than upside down). You could also experiment with adding a pinch of ground cinnamon or nutmeg to your cake batter for a warmer, spicier note, especially if you’re using apples. For those who love a boozy kick, a tiny splash of rum or dark rum extract in the batter or brushed lightly over the pineapple before baking can add a sophisticated depth. If you’re catering to dietary restrictions, remember that with a few simple substitutions – a good quality gluten-free flour blend, plant-based milk and butter, or egg substitutes – these cupcakes can often be adapted to be gluten-free or vegan, ensuring everyone can enjoy a taste of this delicious classic. The beauty of baking is in the creativity, and I encourage you to make this recipe truly your own unique masterpiece!

Your Turn to Bake & Share!

Now that you’re armed with all the tips and inspiration, there’s only one thing left to do: get baking! I’m genuinely excited for you to experience the pure joy and simple satisfaction that comes from creating these incredible treats. Don’t just take my word for it; discover for yourself how effortlessly delicious and impressive these Pineapple Upside Down Cupcakes truly are. They are perfect for bringing to a potluck, delighting your family on a weeknight, or simply treating yourself to a moment of pure, unadulterated sweetness. There’s something incredibly rewarding about flipping those pans and revealing the golden, beautifully caramelized fruit on top of each perfect cupcake. It’s a small moment of magic in your own kitchen!

Once you’ve baked your batch, I would absolutely love to hear about your experience! Did you try any of the serving suggestions? Did you get creative with a unique variation? Perhaps you discovered a new favorite way to enjoy them? Please don’t hesitate to share your thoughts, photos, and any delightful anecdotes in the comments section below. Your feedback and stories are what make this baking community so vibrant and inspiring. Tag me on social media if you share your creations – I’d be thrilled to see your culinary triumphs! So, preheat that oven, gather your ingredients, and prepare to fill your home with the most wonderful aromas and your taste buds with sheer delight. Happy baking, my friends!

Pineapple Upside Down Cupcakes

Pineapple Upside Down Cupcakes are a delightful twist on the classic cake, offering all the joy of the original in perfectly portioned packages. Featuring a caramelized topping of pineapple slices and cherries over a moist, buttery cupcake base, these simple-to-make tropical treats are ideal for any occasion, balancing sweet, fruity flavors with a tender crumb.

Prep Time
30 Minutes

Cook Time
25 Minutes

Total Time
55 Minutes

Servings
12 cupcakes

Ingredients

• 6 tablespoons (85g) unsalted butter, melted
• ½ cup (100g) packed light brown sugar
• 12 slices canned pineapple rings, well-drained
• 12 maraschino cherries, well-drained
• 1 ½ cups (190g) all-purpose flour
• 1 ½ teaspoons baking powder
• ½ teaspoon salt
• ½ cup (113g) unsalted butter, softened
• 1 cup (200g) granulated sugar
• 2 large eggs, room temperature
• 1 teaspoon vanilla extract
• ½ cup (120ml) milk
• Whipped cream or vanilla ice cream (optional garnish)
• Fresh mint leaves (optional garnish)

Instructions

1. Step 1
   Preheat oven to 350°F (175°C). Line a 12-cup muffin tin with paper liners.
2. Step 2
   Melt 6 tablespoons butter and pour evenly into the bottom of each liner. Sprinkle 1 tablespoon brown sugar over butter in each cup.
3. Step 3
   Cut pineapple rings into quarters or halves. Arrange 1-2 pieces of pineapple on top of the brown sugar in each liner. Place a maraschino cherry in the center of each pineapple.
4. Step 4
   In a medium bowl, whisk together flour, baking powder, and salt. Set aside.
5. Step 5
   In a large bowl, cream ½ cup softened butter until light. Gradually add granulated sugar, beating 2-3 minutes until fluffy.
6. Step 6
   Add eggs one at a time, beating until combined after each. Stir in vanilla extract.
7. Step 7
   Alternately add dry ingredients and milk to the wet ingredients in three additions each (dry, milk, dry, milk, dry), mixing on low speed until just combined after each addition. Finish with a gentle fold using a spatula.
8. Step 8
   Spoon batter into prepared liners, filling each two-thirds full.
9. Step 9
   Bake for 20-25 minutes, or until a toothpick inserted into the center (avoiding pineapple) comes out clean.
10. Step 10
    Remove from oven and let cool in the pan for 5-7 minutes. Place a wire rack over the tin and quickly invert. Let sit for 1-2 minutes, then gently lift the muffin tin away and remove liners.
11. Step 11
    Cool completely on the wire rack before serving. Serve warm or at room temperature with optional whipped cream/ice cream and fresh mint. Store leftovers in an airtight container for up to 2 days at room temperature or 3-4 days in the refrigerator.

Important Information

Nutrition Facts (Per Serving)

It is important to consider this information as approximate and not to use it as definitive health advice.

Allergy Information

Please check ingredients for potential allergens and consult a health professional if in doubt.