These Pineapple Upside-Down Cupcakes are a fun, single-servings-sized take on the classic cake, full of tropical flavor. Topped with buttery brown sugar, sweet pineapple and bright maraschino cherries, it creates a delightful caramelized oasis for the fluffy pineapple cake beneath. These cupcakes are ideal for parties or special occasions with their beautiful presentation and irresistible taste!
Why You’ll Love This Recipe:
Tropical Flavors: The pineapple-brown-sugar-maraschino-cherry combination here makes for a tropical flavor classic that’ll make you feel like you’re on vacation with a single bite.
Portion controlled: These cupcakes are already portion controlled, which makes them perfect for potlucks or people on-the-go.
Quick and Simple: With the use of a cake mix, these cupcakes come together quickly and with little effort while still tasting homemade.
Multifaceted: If you are serving them as is, you can add a sprinkle of sugar or a dollop of whipped cream just to be fancy.
Key Ingredients:
Cake Mix: If you can’t find pineapple-flavored cake mix, a yellow cake mix or vanilla cake mix will work, too. For flavor boosters, you can use a teaspoon of pineapple extract.
Maraschino Cherries: If you want, you can substitute the cherries with either fresh or canned pineapple chunks for a top entirely of pineapple.
Instead of butter: For a dairy-free version, replace the butter with margarine or coconut oil. The cupcakes will get an extra hint of tropical flavor from coconut oil.
Pineapple Juice: If you don’t get enough juice from your canned pineapple, you can supplement it with a little water or extra store-bought pineapple juice.
For the full ingredient amounts and instructions, see the recipe card below
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Step-by-Step Instructions
Step 1: Preheat the Oven
Prepare the oven for mixing: preheat it to 350 degrees F (or 175 degrees C).
Prepare the Muffin Cups: Coat 24 muffin cups with cooking spray. This will keep the cupcakes from sticking and allow for easy removal after baking.
Step 2: Prepare the Topping
Melt the Butter: Add 1 teaspoon melted butter into each muffin cup.
Add Brown Sugar and Cherry: Top the butter in each muffin cup with 1 tablespoon of brown sugar, then press a maraschino cherry into the center of the brown sugar.
Crushed Pineapple: Place a heaping tablespoon of well-drained crushed pineapple on top of the cherry and brown sugar layer. Using gentle pressure, work it into a single layer, pressing down so it coats the bottom of each muffin cup.
Step 3: Mix the Cake Batter
Prepare the Batter:
In a big mixing bowl, stir:
1 box of pineapple cake mix
Reserved pineapple juice (from crushed pineapple)
3 eggs
1/3 cup vegetable oil
Mix: Mix on low speed for 30 seconds to moisten. Increase to medium speed and beat for 2 minutes, until the batter is smooth and fully combined.
Step 4: Fill the Muffin Cups
Fill the Muffins: Divide the batter evenly between 8 muffin cups, filling each cup about 2/3 of the way full. This gives the cupcakes room to rise as they bake.
Step 5: Bake the Cupcakes
Bake: Transfer the muffin tin to the preheated oven and bake for around 20 minutes, or until a toothpick inserted into the center of a cupcake comes out clean.
Cautionary Tale: Do not overbake the cake, or the cupcakes’ll dry out.
Step 6: Cool and Invert
Cool a Little: Let the cupcakes cool in the pan for 5 minutes. This gives the topping a little time to set, which helps it to invert better, without coming spilling out.
Invert the Cupcakes: Dust a knife around the edge of each cupcake to loosen them. Gently turn the muffin tin upside down over a wax-paper-lined baking sheet. Your pineapple and brown sugar topping would be beautiful.
Step 7: Dust with Sugar
Dust with Confectioners’ Sugar: If you want their sweet, fluffy tops to have a pretty finish (as well as a little extra sweetness), lightly dust them with confectioners’ sugar before serving.
Serving Suggestions:
These Pineapple Upside-Down Cupcakes are best eaten warm but delicious at room temperature too. Here are some ideas for how to serve them:
With Ice Cream: Serve each cupcake with a scoop of vanilla ice cream for a classic pairing. The cold, creamy ice cream balances with the warm, caramelized pineapple.
Whipped Cream: Add a dollop of whipped cream to each cupcake for a light fluffy addition.
Toasted Coconut: Add a handful of toasted coconut flakes on top of the cupcakes for a crunchy, tropical touch.
Storage and Reheating Tips:
To store: Place any leftover cupcakes in an airtight container and place in refrigerator for up to 3 days. For a cold dish or warmed as can be the case.
To reheat: Microwave for 15-20 seconds or place in a 350°F (175 °C) oven for 5 minutes to warm.
They freeze well: These cupcakes freeze great! Wrap each cupcake tightly in plastic wrap, place in a freezer-safe container, and freeze for up to 3 months. Defrost overnight in the refrigerator before serving.
Recipe Variations:
Pineapple and Coconut Cupcakes: Mix in 1/2 cup shredded coconut to the cake batter for another dose of tropical flavor.
Rum-Spiked Topping: For an adult rendition, whisk a tablespoon of dark rum into the melted butter and brown sugar mixture for a Pina Colada-inspired pudding.
Mini Pineapple Upside-Down Cupcakes: These bite-sized versions of a classic cake call for a mini muffin tin. Simply lower the baking time to around 12 to 15 minutes.
Conclusion:
These Pineapple Upside-Down Cupcakes deliver all the classic flavors of that traditional cake but in a fun, single-serve size. With a sweet, buttery crust and moist, pineapple-filled cake, they’re equally good slathered in a layer of whipped cream for summer barbecues and holiday desserts alike. Once you make these, they will definitely become a regular in your dessert rotation!
Pineapple Upside-Down Cupcakes
Ingredients
- 1/2 cup melted butter for the topping
- 1 1/2 cups brown sugar for the topping
- 24 maraschino cherries
- 1 (20 oz) can crushed pineapple well-drained
- 1 (18.25 oz) package pineapple cake mix such as Duncan Hines® Pineapple Supreme
- 1 1/3 cups pineapple juice reserved from the crushed pineapple
- 3 large eggs
- 1/3 cup vegetable oil
- 1 tbsp confectioners' sugar optional, for dusting
Instructions
- Preheat your oven to 350°F (175°C) and spray 24 muffin cups with cooking spray.
- Place 1 teaspoon of melted butter into each muffin cup. Add 1 tablespoon of brown sugar on top of the butter, then press a maraschino cherry into the center. Spoon a heaping tablespoon of crushed pineapple over the cherry and brown sugar mixture, pressing down gently to create an even layer.
- In a large mixing bowl, combine the pineapple cake mix, reserved pineapple juice, eggs, and vegetable oil. Mix on low speed for 30 seconds, then increase speed to medium and beat for 2 minutes until smooth.
- Pour the prepared cake batter into the muffin cups, filling each about 2/3 full.
- Bake in the preheated oven for about 20 minutes, or until a toothpick inserted into the center comes out clean.
- Let the cupcakes cool in the pan for 5 minutes. Run a knife around the edges to loosen them, then carefully invert the muffin tin onto a baking sheet lined with wax paper.
- For an extra touch of sweetness, dust the tops of the cupcakes with confectioners' sugar before serving.