Go Back
Easy Pineapple Upside-Down Cupcakes Recipe

Easy Pineapple Upside-Down Cupcakes

These 24 easy pineapple upside-down cupcakes feature tender yellow cake beneath a buttery brown sugar, pineapple, and maraschino cherry topping. They bake quickly and are inverted while warm so the caramelized fruit releases from the muffin pan.
Print Recipe Pin Recipe
Prep Time 20 minutes
Cook Time 20 minutes
Total Time 45 minutes
Servings: 24 servings
Ingredients Method Notes

Ingredients
  

Pineapple Topping
  • 1 20-ounce can Pineapple chunks, drained and finely chopped
  • 1/2 cup (113 g) Unsalted butter, melted
  • 1 cup (200 g) Packed light brown sugar
  • 24 cherries Maraschino cherries, drained
Cake Batter
  • 1 box, about 15.25 ounces (432 g) Yellow cake mix
  • 3 eggs Large eggs
  • 1/3 cup (80 ml) Canola or vegetable oil
  • 1 1/3 cups (320 ml) Water

Method
 

Step-by-Step
  1. Heat the oven to 350°F (175°C) and generously grease all 24 standard muffin cups. Coat the bottoms and sides thoroughly because the butter and brown sugar topping becomes sticky as it bakes.
  2. Drain the pineapple chunks well, then finely chop them into small pieces. Set the pineapple aside while you prepare the muffin pan and cake batter.
  3. Spoon approximately 1 teaspoon of melted butter into each muffin cup. Sprinkle about 2 teaspoons of packed light brown sugar over the butter in every cup.
  4. Place one drained maraschino cherry in the center of each cup, then distribute the chopped pineapple evenly over the brown sugar. Try to keep the fruit in an even layer so each cupcake has a balanced topping.
  5. Prepare the yellow cake mix with the three eggs, canola or vegetable oil, and water according to the package-style batter directions. Beat until smooth, usually about 2 minutes, scraping the bowl once if needed.
  6. Spoon the batter over the fruit mixture, filling each muffin cup about two-thirds full. Avoid overfilling, since the batter needs room to rise without spilling over the edges.
  7. Bake for 20 to 25 minutes, until the cake tops are golden and a toothpick inserted into the cake portion comes out clean. Do not test directly through the fruit topping, as pineapple or melted sugar can make the toothpick look wet.
  8. Let the cupcakes cool in the pan for about 5 minutes. Run a thin knife around the edges, place a serving tray over the muffin pan, and carefully invert the cupcakes while they are still warm.

Notes

Grease the muffin pan very thoroughly, especially around the sides and bottoms. Invert the cupcakes after about 5 minutes of cooling; if they cool completely in the pan, the sugar topping is more likely to harden and stick.