Pineapple Upside Down Cupcakes
There’s something whimsical about the way Pineapple Upside Down Cupcakes transform a classic dessert into a playful treat. Growing up, I remember my grandma making her famous pineapple upside-down cake for family gatherings, and the joy it brought to our table. As I adapted her recipe into cupcake form, I found that individual portions create a fun experience for everyone. Each cupcake is a delightful surprise, with tender cake perched atop juicy pineapple, all crowned with a maraschino cherry. These cupcakes are perfect for celebrations, picnics, or simply to satisfy a sweet craving. Whether it’s a sunny afternoon or a cozy evening at home, Pineapple Upside Down Cupcakes always brighten the mood and bring back fond memories. Trust me, once you make these, they will quickly become a beloved favorite!
Recipe Snapshot
50 mins
25 mins
25 mins
Medium
230 kcal
2g g
Gluten-Free, Low FODMAP
10g g
Wooden Spoon, Mixing Bowl, Frying Pan, Whisk, Baking Sheet, Food Processor, Oven
The Beauty of This Pineapple Upside Down Cupcakes
1. Childhood Nostalgia
The moment you take a bite of Pineapple Upside Down Cupcakes, you’re instantly transported back to family gatherings and summer picnics. The combination of sweet pineapple and moist cake evokes warm memories and a sense of comfort.
2. Individual Serving Size
Unlike traditional cakes, these cupcakes allow for easy serving without the need for slicing. Each person gets their own portion, making them perfect for parties or potlucks.
3. A Moist and Flavorful Treat
The juicy pineapple chunks nestled in the cupcake create a beautiful contrast to the fluffy cake, keeping each bite moist and flavorful. It’s a winning combo that never disappoints!
4. Versatile and Adaptable
You can easily customize Pineapple Upside Down Cupcakes by adding your favorite spices, like cinnamon or nutmeg, to the batter for an extra flavor kick. You can also experiment with different fruits or toppings.
5. Simple and Fun to Make
This recipe is straightforward and perfect for baking novices and seasoned bakers alike. It’s a fun activity to do with kids or friends, making the process as enjoyable as the final result.
Everything You Need for Pineapple Upside Down Cupcakes

Creating Pineapple Upside Down Cupcakes is all about using the right ingredients that harmonize beautifully together. The key players include sweet pineapple, rich butter, and fluffy all-purpose flour. The combination of these ingredients not only ensures a yummy treat but also creates a delightful texture.
- Pineapple chunks in pineapple juice (20 oz): These provide the sweet base for the cupcakes. Their juice is also used in the batter for added flavor.
- Pineapple chunks in pineapple juice (8 oz): Extra pineapple for those who can’t get enough! These are layered on top for a beautiful presentation.
- Light brown sugar: This adds a lovely caramel flavor and moisture to the cupcakes, enhancing their sweetness.
- Unsalted butter: Essential for rich flavor and a tender crumb.
- All-purpose flour: The backbone of the cupcake, giving it structure.
- Granulated sugar: Balances the flavors and helps with the cupcake’s rise.
- Baking powder: The leavening agent that ensures the cupcakes rise beautifully.
- Salt: A little salt enhances the sweetness of the cupcakes and balances the flavors.
- Large egg: Provides richness and helps bind the ingredients together.
- Pineapple juice: Adds moisture and a tropical flavor to the batter.
- Vanilla extract: A classic flavoring that complements the pineapple beautifully.
- Heavy cream: This is whipped for the topping, adding a rich and creamy finish.
- Granulated sugar (for whipped cream): Sweetens the whipped cream, making it the perfect topping.
- Maraschino cherries: The classic garnish that adds a pop of color and sweetness on top.
How to Assemble Pineapple Upside Down Cupcakes

Making Pineapple Upside Down Cupcakes is a delightful process filled with fragrant ingredients and sweet anticipation. Follow these simple steps to create your own mini masterpieces!
- Preheat your oven to 350 degrees. Make sure to spray 12 muffin cups generously with non-stick cooking spray to ensure those cupcakes release easily.
- Drain both cans of the pineapple chunks, reserving half a cup of the juice for the batter. Place the pineapple on several layers of paper towels to absorb excess moisture. This step is important to prevent soggy cupcakes.
- In a microwave-safe bowl, melt one-third cup of unsalted butter. Once melted, stir in the light brown sugar until it’s well combined and syrupy. This mixture will form the delicious base for your cupcakes.
- Divide this brown sugar mixture evenly among the muffin wells, adding about two teaspoons to each. Follow this by arranging pineapple chunks on top of the sugar mixture; aim for about five pieces in each well.
- In a mixing bowl, whisk together all-purpose flour, granulated sugar, baking powder, and salt until well combined.
- Now, attach your mixer with a paddle attachment and add unsalted butter and the reserved pineapple juice into the flour mixture. Mix until the batter is smooth and well combined, which should take about one to two minutes.
- Add in the large egg and vanilla extract, mixing until these are fully incorporated into the batter.
- Carefully divide the batter evenly among the muffin cups, layering it on top of the pineapple chunks, making sure to cover them completely.
- Bake in your preheated oven for approximately 23 to 26 minutes, or until a toothpick inserted into the center comes out clean. As the cupcakes bake, your kitchen will fill with the most inviting aroma!
- Once baked, remove the cupcakes from the oven and let them cool for five minutes. Then, run a sharp knife around the edges to loosen them from the pan.
- Place a wire cooling rack over the top of the muffin pan and carefully flip it to invert the cupcakes onto the wire rack. Let them cool completely.
- While the cupcakes are cooling, prepare the sweetened whipped cream. In another bowl, whip heavy cream using an electric mixer on high speed until soft peaks form. Add in granulated sugar and continue to whip until stiff peaks form.
- Just before serving, pipe the whipped cream over the cooled cupcakes and top each with a maraschino cherry for that perfect finishing touch!
Things Worth Knowing
- Make it in advance: You can prepare the cupcakes a day ahead. Just store them in an airtight container at room temperature. Add whipped cream just before serving.
- Oven temperature: Always preheat your oven. This helps the cupcakes rise properly and cook evenly.
- Testing doneness: Use a toothpick to test for doneness. It should come out clean or with just a few crumbs attached.
- Cooling time: Allow the cupcakes to cool before inverting them. This helps them maintain their shape and prevents tearing.
Recipe Variations about Pineapple Upside Down Cupcakes

There are so many exciting ways to put a unique spin on Pineapple Upside Down Cupcakes. Here are some ideas to inspire your creativity!
- Storage: To store leftovers, keep the cupcakes in an airtight container at room temperature for up to three days, or in the refrigerator for up to a week.
- Freezing: Yes, you can freeze these cupcakes! Place them in an airtight container or freezer bag and freeze for up to three months. Thaw in the fridge overnight before enjoying.
- Fruit variations: Instead of pineapple, try using peaches or cherries for a seasonal twist!
- Frosting options: Instead of whipped cream, consider using cream cheese frosting for a tangy flavor contrast.
- Serving suggestions: These cupcakes pair beautifully with vanilla ice cream or a scoop of sorbet to balance the sweetness.
- Decorative touches: Feel free to add toasted coconut on top for a tropical flair!
Pairing Suggestions for Pineapple Upside Down Cupcakes
When serving your Pineapple Upside Down Cupcakes, consider these pairing suggestions to elevate your dessert experience:
- Seasonal fruits: Serve with fresh berries or sliced mango on the side for a refreshing contrast.
- Whipped cream: A dollop of homemade whipped cream enhances the sweetness and adds a creamy texture.
- Coffee or tea: Pair these cupcakes with a cup of coffee or tea for a delightful afternoon treat.
- Picnic treats: These cupcakes are perfect for outdoor gatherings, served alongside fresh fruit salads and lemonade.
- Birthday celebrations: They make a whimsical addition to any birthday party, especially when decorated with colorful sprinkles.
- Storage tips: Keep any leftover cupcakes in an airtight container at room temperature for up to three days.
FAQ
Conclusion
In conclusion, Pineapple Upside Down Cupcakes bring a taste of nostalgia and joy to any gathering. Their individual servings make them not only visually appealing but also perfect for sharing. I encourage you to give this recipe a try and delight your family and friends with these sweet treats. They’re a wonderful way to create new memories, just like the ones I cherish from my childhood. Happy baking!

Pineapple Upside Down Cupcakes
Equipment
- Wooden Spoon
- Mixing Bowl
- Frying Pan
- Whisk
- Baking Sheet
- Food Processor
- Oven
Ingredients
- 1 can (20 oz) Pineapple chunks in pineapple juice
- 1 can (8 oz) Pineapple chunks in pineapple juice
- 1/3 cup Light brown sugar
- 1/3 cup Unsalted butter
- 1 cup All-purpose flour
- 3/4 cup Granulated sugar
- 1/2 tsp Baking powder
- 1/4 tsp Salt
- 1/4 cup Unsalted butter, softened
- 1/2 cup (4 oz) Pineapple juice (from pineapple chunk can)
- 1 large Egg
- 1/2 tsp Vanilla extract
- 3/4 cup Heavy cream
- 2 Tbsp Granulated sugar
- 12 Maraschino cherries
Instructions
- Preheat your oven to 350 degrees. Make sure to spray 12 muffin cups generously with non-stick cooking spray to ensure those cupcakes release easily.
- Drain both cans of the pineapple chunks, reserving half a cup of the juice for the batter. Place the pineapple on several layers of paper towels to absorb excess moisture. This step is important to prevent soggy cupcakes.
- In a microwave-safe bowl, melt one-third cup of unsalted butter. Once melted, stir in the light brown sugar until it’s well combined and syrupy. This mixture will form the delicious base for your cupcakes.
- Divide this brown sugar mixture evenly among the muffin wells, adding about two teaspoons to each. Follow this by arranging pineapple chunks on top of the sugar mixture; aim for about five pieces in each well.
- In a mixing bowl, whisk together all-purpose flour, granulated sugar, baking powder, and salt until well combined.
- Now, attach your mixer with a paddle attachment and add unsalted butter and the reserved pineapple juice into the flour mixture. Mix until the batter is smooth and well combined, which should take about one to two minutes.
- Add in the large egg and vanilla extract, mixing until these are fully incorporated into the batter.
- Carefully divide the batter evenly among the muffin cups, layering it on top of the pineapple chunks, making sure to cover them completely.
- Bake in your preheated oven for approximately 23 to 26 minutes, or until a toothpick inserted into the center comes out clean. As the cupcakes bake, your kitchen will fill with the most inviting aroma!
- Once baked, remove the cupcakes from the oven and let them cool for five minutes. Then, run a sharp knife around the edges to loosen them from the pan.
- Place a wire cooling rack over the top of the muffin pan and carefully flip it to invert the cupcakes onto the wire rack. Let them cool completely.
- While the cupcakes are cooling, prepare the sweetened whipped cream. In another bowl, whip heavy cream using an electric mixer on high speed until soft peaks form. Add in granulated sugar and continue to whip until stiff peaks form.
- Just before serving, pipe the whipped cream over the cooled cupcakes and top each with a maraschino cherry for that perfect finishing touch!
Notes
- Tip 1: To store leftovers, keep the cupcakes in an airtight container at room temperature for up to three days, or in the refrigerator for up to a week.
- Tip 2: Yes, you can freeze these cupcakes! Place them in an airtight container or freezer bag and freeze for up to three months. Thaw in the fridge overnight before enjoying.
- Tip 3: Instead of pineapple, try using peaches or cherries for a seasonal twist!
- Tip 4: Instead of whipped cream, consider using cream cheese frosting for a tangy flavor contrast.
- Tip 5: These cupcakes pair beautifully with vanilla ice cream or a scoop of sorbet to balance the sweetness.
