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Three pineapple upside-down cupcakes on a white plate, each topped with a caramelized pineapple ring and a bright red maraschino cherry in the center.

Pineapple Upside Down Cupcakes

A beautiful, nostalgic individual-sized twist on a classic Southern dessert featuring a light, airy vanilla sponge cake baked over a sticky brown sugar caramel glaze, topped with a glistening pineapple ring and a sweet maraschino cherry.
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Prep Time 15 minutes
Cook Time 20 minutes
Total Time 35 minutes
Servings: 4 people
Course: Dessert
Cuisine: Southern
Calories: 280
Ingredients Equipment Method Notes

Ingredients
  

  • 1.5 cups all-purpose flour sifted well to build a light, tender structural yellow cake crumb
  • 1.5 teaspoons baking powder vital for delivering a beautiful pillowy rise to the sponge layers
  • 12 slices canned pineapple packed in juice; patted completely dry and trimmed to fit the cup floors
  • 12 pieces maraschino cherries stems removed; positioned snugly inside the center of each fruit ring
  • ½ cup unsalted butter divided cleanly for the gooey brown sugar glaze base and the cake dough
  • ⅔ cup light brown sugar packed tightly to melt into a glossy rich caramel mirror top
  • ¾ cup granulated sugar blended into the cake batter to sweeten the crumb structure smoothly

Equipment

  • 1 Metal Muffin Tin Standard 12-count baking pan used to shape the individual cakes cleanly
  • 1 Electric Hand Mixer Essential for creaming the softened butter and sugar into a light, voluminous base
  • 1 Silicone Spatula To gently fold the dry flour trails and liquid juices together with a soft touch

Method
 

  1. Line a standard 12-count metal muffin tin with premium parchment liners and distribute a half-teaspoon of melted butter inside each well.
  2. Spoon a tablespoon of packed light brown sugar cleanly over the melted butter floor inside each individual cup liner.
  3. Pat the canned pineapple slices completely dry with paper towels, trim to fit, and lay one wheel flat over the sugar bed.
  4. Nest a stemless maraschino cherry snugly right inside the exact center opening of each fruit wheel to anchor the canopy layout.
  5. Whisk the sifted flour, baking powder, and salt together inside a bowl, while creaming the remaining butter and sugar in a separate container.
  6. Beat the eggs into the creamed sugar, alternating streams of vanilla, pineapple juice, and flour mix just until uniform.
  7. Spoon the thick batter over the arranged fruit canopies, smoothing the tops, and bake at 350°F for twenty minutes until golden brown.
  8. Let the pan rest for five minutes, invert a flat platter over top, flip confidently, and peel off the liners to reveal the glistening fruit crown.

Notes

Pat the canned pineapple slices completely bone-dry with paper towels before placing them inside the liners to prevent the caramel glaze from turning watery. Invert the baking pan onto a platter exactly five minutes after removing it from the oven to ensure the sticky fruit canopy drops cleanly without sticking.