Pineapple Upside-Down Cupcakes Recipe
If you’re searching for a tropical treat that’s both charming and utterly irresistible, Pineapple Upside-Down Cupcakes are about to become your new favorite dessert. Imagine the classic retro cake, but in adorable, single-serve form! Each cupcake bursts with glossy caramelized pineapple, a ruby-red cherry, and a soft, buttery crumb that’s as cheerful as a summer day. This recipe takes everything you love about the traditional upside-down cake and transforms it into hand-held delights perfect for sharing, gifting, or savoring all to yourself.
Ingredients You’ll Need
These Pineapple Upside-Down Cupcakes come together with a handful of simple ingredients, each playing a vital role in crafting their signature flavor and eye-catching appearance. From the lush pineapple to the golden cake, every element has its moment to shine.
- Unsalted Butter (1/4 cup, melted): Provides rich flavor and helps create that luscious, caramel-like topping.
- Brown Sugar (1/2 cup, packed): Adds deep sweetness and helps the pineapple and cherries caramelize beautifully.
- Pineapple Slices (1 20-ounce can, cut into small chunks): Offers bright, juicy bursts of tropical flavor and a pop of sunshine in each bite.
- Maraschino Cherries (12, halved): Bring a touch of color and a sweet-tart finish that’s classic to this dessert.
- Yellow Cake Mix (1 box, plus eggs, oil, and water as listed on the box): Makes prep a breeze while yielding a soft, moist crumb every time.
How to Make Pineapple Upside-Down Cupcakes
Step 1: Prep the Muffin Tin
Start by preheating your oven to 350°F and giving your 12-cup muffin tin a light coating of nonstick spray. Skip the cupcake liners for this recipe—direct contact with the pan is what helps the brown sugar and butter create that irresistible golden topping.
Step 2: Build the Caramel Base
In a small bowl, combine the melted butter and packed brown sugar. Spoon roughly 1 tablespoon of this sweet, buttery mixture into the bottom of each muffin cup. This layer is the secret to the cupcakes’ glossy, caramelized tops once flipped!
Step 3: Add the Fruit
Nestle a few pineapple chunks on top of the brown sugar layer in each cup, then place half a maraschino cherry (cut side up) right in the center. The pineapple brings a burst of tropical tang, while the cherry adds that iconic pop of color and flavor.
Step 4: Mix and Fill with Cake Batter
Prepare your yellow cake mix according to the package instructions—usually with eggs, oil, and water. Once the batter is smooth, fill each muffin cup about three-quarters full. This gives the cupcakes room to rise and set perfectly without overflowing.
Step 5: Bake to Perfection
Slide the muffin tin into the oven and bake for 20 to 25 minutes. You’ll know they’re ready when a toothpick inserted in the center comes out clean and the tops are lightly golden. The aroma at this stage will be pure nostalgia!
Step 6: Cool and Invert
Let the cupcakes cool in the pan for 5 minutes—just enough time for the syrupy topping to set a bit. Then, run a knife around the edges to loosen, and carefully invert each cupcake onto a wire rack or platter. The magic moment is seeing that glistening pineapple-cherry crown!
How to Serve Pineapple Upside-Down Cupcakes
Garnishes
For a festive finish, add a tiny dollop of whipped cream or a sprinkle of toasted coconut right before serving. A fresh mint leaf makes a pretty, fragrant accent that pairs beautifully with the tropical flavors.
Side Dishes
These cupcakes are delightful alongside a scoop of vanilla ice cream or a fresh fruit salad. If you’re serving them at a brunch, they’re lovely with a citrusy mimosa or a cool glass of iced tea.
Creative Ways to Present
Arrange the Pineapple Upside-Down Cupcakes on a tiered dessert stand for a party, or wrap each one individually in wax paper and tie with a ribbon for sweet, portable gifts. They also make a playful addition to a dessert buffet, nestled among other mini treats.
Make Ahead and Storage
Storing Leftovers
Store any leftover cupcakes in an airtight container at room temperature for up to 2 days. If your kitchen is warm, you may want to refrigerate them to keep the fruit fresh and the topping just right.
Freezing
You can freeze Pineapple Upside-Down Cupcakes for up to one month. Once completely cooled, wrap each cupcake tightly in plastic wrap and then place in a freezer-safe bag or container. Thaw overnight in the fridge before serving.
Reheating
To reheat, simply pop a cupcake in the microwave for about 10 to 15 seconds, just until warmed. This brings back the gooey, caramelized topping and makes them taste freshly baked.
FAQs
Can I use fresh pineapple instead of canned?
Absolutely! Just be sure to cut your fresh pineapple into small chunks and pat them dry to prevent excess moisture from making the cupcakes soggy.
What if I don’t have maraschino cherries?
You can skip them or substitute with candied cherries, but the classic look and flavor really shine with maraschinos. Even a dab of cherry preserves can work in a pinch!
Can I make these Pineapple Upside-Down Cupcakes gluten free?
Yes, simply use your favorite gluten-free yellow cake mix and follow the package instructions. The rest of the ingredients are naturally gluten free.
How do I keep the cupcakes from sticking to the pan?
Make sure to grease your muffin tin well and let the cupcakes cool for just a few minutes before inverting. Running a thin knife around the edges helps release any sticky, caramelized bits.
Can I make mini Pineapple Upside-Down Cupcakes in a mini muffin tin?
Definitely! Just reduce the baking time and use smaller pieces of pineapple and cherry. They’re perfect bite-sized treats for parties or potlucks.
Final Thoughts
If you’re craving a dessert that brings instant smiles and a taste of sunshine, you can’t go wrong with Pineapple Upside-Down Cupcakes. They’re easy, nostalgic, and always a crowd-pleaser—so gather your ingredients and treat yourself (and your loved ones) to a sweet, tropical twist on a classic favorite!
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Pineapple Upside-Down Cupcakes Recipe
- Total Time: 40 minutes
- Yield: 12 cupcakes 1x
- Diet: Vegetarian
Description
Delight in these Pineapple Upside-Down Cupcakes, a tropical twist on the classic dessert that combines caramelized brown sugar, juicy pineapple, and maraschino cherries atop moist yellow cake batter. Perfectly portioned as individual cupcakes, they offer a fun and easy way to enjoy the flavors of a traditional pineapple upside-down cake with minimal effort and maximum flavor.
Ingredients
Topping
- 1/4 cup unsalted butter (melted)
- 1/2 cup brown sugar (packed)
- 1 (20-ounce) can pineapple slices, cut into small chunks
- 12 maraschino cherries (halved)
Cake Batter
- 1 box yellow cake mix
- Ingredients listed on the cake mix box (usually eggs, oil, and water)
Instructions
- Preheat and Prepare Muffin Tin: Preheat your oven to 350°F (175°C). Lightly grease a 12-cup muffin tin thoroughly; do not use cupcake liners to allow easy inversion later.
- Mix Butter and Brown Sugar: In a small bowl, combine the melted unsalted butter with the packed brown sugar, mixing well until combined.
- Add Topping to Muffin Cups: Spoon about 1 tablespoon of the butter-brown sugar mixture into the bottom of each muffin cup to create a caramel base.
- Place Pineapple and Cherry Pieces: Arrange a few small pineapple chunks on top of the sugar mixture in each cup, then add half a maraschino cherry (with the cut side facing up) over the pineapple to decorate.
- Prepare Cake Batter: Following the instructions on the yellow cake mix box, prepare the batter by adding required eggs, oil, and water and mixing until smooth.
- Fill Muffin Cups with Batter: Pour the prepared cake batter into each muffin cup, filling approximately three-quarters full to give the cupcakes room to rise.
- Bake Cupcakes: Place the muffin tin in the oven, baking for 20 to 25 minutes or until a toothpick inserted into the center of a cupcake comes out clean.
- Cool and Invert: Allow the cupcakes to cool in the pan for 5 minutes. Then, carefully run a knife around the edges of each cupcake to loosen them. Invert the cupcakes onto a wire rack or tray so the pineapple topping is on top.
- Serve: Serve the cupcakes warm or at room temperature for the best flavor and texture.
Notes
- If using pineapple tidbits or crushed pineapple instead of slices, ensure they are well-drained to prevent sogginess in the cupcakes.
- These cupcakes are best enjoyed the day they are made for optimum freshness and texture.
- You can store leftover cupcakes covered at room temperature for up to 2 days.
- Prep Time: 15 minutes
- Cook Time: 25 minutes
- Category: Dessert
- Method: Baking
- Cuisine: American
Nutrition
- Serving Size: 1 cupcake
- Calories: 260
- Sugar: 25g
- Sodium: 280mg
- Fat: 10g
- Saturated Fat: 3g
- Unsaturated Fat: 6g
- Trans Fat: 0g
- Carbohydrates: 39g
- Fiber: 1g
- Protein: 2g
- Cholesterol: 35mg
