These Pineapple Upside Down Cupcakes are everything people love about the classic cake, just scaled down into adorable, perfectly portioned treats. The tops bake into a glossy layer of buttery brown sugar, tender pineapple, and bright cherries that look bakery-worthy the moment you flip them out of the pan. The cake itself stays soft and moist, thanks to the pineapple juice mixed right into the batter.
I’ll be honest; the first time I made these, I hovered nervously when it came time to turn them out. But they released cleanly, held their shape, and honestly looked beautiful. The combination of warm caramelized fruit and fluffy yellow cake is nostalgic in the best way, and the individual size makes them feel extra special without extra work.
These are perfect for family gatherings, potlucks, or anytime you want a dessert that feels a little fun and celebratory. They’re especially good served warm, when the brown sugar topping is still soft and gooey. Love this recipe? Pin it to your dessert board on Pinterest so you don’t lose it!
Pineapple Upside Down Cupcakes
Course: DessertsCuisine: AmericanDifficulty: Easy24
cupcakes20
minutes25
minutes230
kcalDescription: Individual pineapple upside down cakes with caramelized fruit and tender yellow cake.
Ingredients
40 oz canned pineapple slices, drained, juice reserved (1 cup)
1 box yellow cake mix
½ cup vegetable oil
3 large eggs
⅓ cup butter, melted
⅔ cup brown sugar, packed
12 maraschino cherries, halved
Directions
- Preheat the oven to 180°C / 350°F. Generously spray 24 standard muffin cups with cooking spray.
- Cut each pineapple slice into 4 even pieces and set aside.
- In a large mixing bowl, combine the cake mix, vegetable oil, eggs, and 1 cup reserved pineapple juice. Beat on low speed for 30 seconds, then on medium speed for 2 minutes, scraping down the bowl as needed.
- In a small bowl, stir together the melted butter and brown sugar until smooth. Spoon about 1½ teaspoons of the mixture into the bottom of each muffin cup, spreading it evenly.
- Arrange 3 pineapple pieces over the brown sugar mixture in each cup, adjusting as needed based on pan size. Place half a maraschino cherry, cut side up, in the center of the pineapple.
- Spoon about ¼ cup of cake batter over the fruit in each muffin cup.
- Bake for 20 to 25 minutes, or until a toothpick inserted into the cake comes out clean.
- Let the cupcakes cool for 5 minutes. Run a knife gently around the edges, then invert onto a baking sheet to release. Serve warm or at room temperature.
Cooking Notes
- Do not overfill the muffin cups; sticking to ¼ cup batter helps prevent overflow.
- Turning the cupcakes out while still warm ensures the topping releases cleanly.
- If any fruit sticks, simply spoon it back onto the cupcake while warm.
Nutrition
Estimated Nutrition per Serving
- Calories: 230 kcal
- Fat: 11 g
- Carb: 32 g
- Protein: 3 g
Yields: 24 cupcakes
Recipe Science
Pineapple upside down cupcakes rely on sugar caramelization and controlled moisture to achieve their signature texture and appearance. The brown sugar and butter melt together during baking, forming a syrup that thickens as water evaporates and sugars concentrate. This creates a glossy topping that adheres to the fruit once inverted.
Using pineapple juice in the batter adds moisture and mild acidity, which helps tenderize the crumb while enhancing fruit flavor. Commercial cake mixes are formulated to handle added liquid without collapsing, making them ideal for fruit-based variations like this one.
From a practical standpoint, these cupcakes cool and set quickly, allowing the topping to stabilize before serving. Sugar content per cupcake is moderate-high; pairing with fresh fruit or serving smaller portions can help balance overall intake.
Why You’ll Love This Recipe
- No Slicing Needed: Individual portions make serving effortless.
- Beautiful Presentation: Each cupcake looks finished and festive.
- Classic Flavor: All the nostalgia of pineapple upside down cake.
- Beginner-Friendly: Reliable results with simple steps.
FAQ
- Can I use fresh pineapple?
Yes, but canned pineapple provides consistent sweetness and moisture. - Do these need to be served warm?
They’re best warm, but also delicious at room temperature. - Can I make them ahead?
Yes; store covered at room temperature for up to 24 hours. - What if my cupcakes stick?
Let them sit inverted for a minute, then gently lift the pan.
Conclusion
These pineapple upside down cupcakes are proof that classic desserts can still feel fun and fresh. Don’t stress about perfection; the charm is in their homemade look and flavor. What’s your favorite retro dessert you’d love to see turned into cupcakes?
