These Pineapple Upside Down Cupcakes transform the beloved retro dessert into perfectly portioned individual treats. Each cupcake features a crown of caramelized pineapple and cherry nested in a brown sugar glaze, sitting atop a tender, pineapple-infused vanilla cake. They deliver all the classic flavors you love about traditional pineapple upside-down cake but in a convenient, portable format that’s perfect for any occasion. These charming treats combine nostalgia with modern convenience, making them an irresistible addition to your dessert repertoire.
Pineapple Upside Down Cupcakes: Individual Bites of Retro Charm
Pineapple Upside Down Cupcakes take everything wonderful about the classic cake and transform it into perfectly portioned, individually-sized treats. These charming cupcakes feature the same beloved combination of caramelized pineapple, maraschino cherries, and buttery brown sugar topping that made the original cake famous, but in a more versatile and entertaining format that’s perfect for modern gatherings and portion control.
What makes these cupcakes truly special is their perfect balance of flavors and textures. Each bite delivers the warm, gooey caramel topping that mingles with tender pineapple rings and sweet cherries, all sitting atop a light, moist vanilla cake that’s been infused with pineapple juice. The individual portions ensure that every cupcake has the perfect ratio of topping to cake, and each guest gets their own complete miniature upside-down cake experience.
Why You Should Try This Recipe
The genius of this recipe lies in its ability to solve common problems associated with traditional pineapple upside-down cake. No more fighting over corner pieces or dealing with messy slicing – each cupcake is its own perfect serving. The smaller size also means faster baking time and more consistent results. Plus, the individual portions make these treats ideal for buffets, bake sales, or any situation where plated desserts aren’t practical.
Nostalgic Charm in Cupcake Form
These cupcakes aren’t just delicious; they’re also conversation starters. Their retro-chic appearance brings a touch of nostalgia to any dessert table while their miniature size adds an element of modern charm. They’re perfect for everything from casual family gatherings to elegant parties, and they never fail to delight guests of all ages.
Storage Options
- Room Temperature: Up to 2 days in airtight container
- Refrigerator: Up to 5 days
- Freezer: Up to 2 months (unglazed)
- Best served: Slightly warm or room temperature
- Reheat: 10-15 seconds in microwave
Summary
- Prep Time: 25 minutes
- Cook Time: 20-22 minutes
- Total Time: 45 minutes
- Yield: 12 cupcakes
- Difficulty Level: Intermediate
Equipment
- 12-cup muffin tin
- Cupcake liners (optional)
- Mixing bowls
- Electric mixer
- Measuring cups and spoons
- Small saucepan
- Rubber spatula
- Wire cooling rack
- Sharp knife
- Can opener
- Small spoon for topping
Ingredients
For the Topping:
- 1/2 cup butter, melted
- 1 cup brown sugar, packed
- 1 (20 oz) can pineapple rings, drained and cut into quarters
- 12 maraschino cherries, halved
- Reserved pineapple juice
For the Cake:
- 1 1/2 cups all-purpose flour
- 1 1/2 teaspoons baking powder
- 1/4 teaspoon salt
- 1/2 cup butter, softened
- 1 cup granulated sugar
- 2 large eggs
- 1 teaspoon vanilla extract
- 1/2 cup milk
- 1/4 cup reserved pineapple juice
Instructions
- Preheat oven to 350°F. Grease a 12-cup muffin tin generously.
- Prepare the topping:
- Mix melted butter with brown sugar
- Spoon about 1 tablespoon mixture into each muffin cup
- Place 2-3 pineapple pieces in each cup
- Add cherry half in center of each cup
- Make the cake batter:
- Whisk together flour, baking powder, and salt
- In another bowl, cream butter and sugar until light and fluffy
- Beat in eggs one at a time
- Add vanilla extract
- Alternate adding dry ingredients and mixed milk/pineapple juice
- Assemble and bake:
- Spoon batter over topping in each cup, filling 2/3 full
- Tap pan gently to remove air bubbles
- Bake 20-22 minutes until toothpick comes out clean
- Finish cupcakes:
- Let cool in pan for 5 minutes
- Run knife around edges of each cupcake
- Place wire rack over pan and invert quickly
- Let cupcakes cool completely
Notes
- Use fresh pineapple if preferred, but canned ensures consistent results
- Don’t overfill cups – batter will rise
- Grease muffin tin well, even if using liners
- Save excess pineapple juice for the cake batter
- Cool only 5 minutes before inverting to prevent sticking
- Pat pineapple pieces dry to prevent excess moisture
- Can substitute pineapple rings with crushed pineapple
- Test doneness with toothpick in cake portion, not topping
- For extra flavor, add 1/2 teaspoon rum extract
- Make sure brown sugar mixture is spread evenly