Duncan Hines Pineapple Upside Down Cake – A Retro Classic Made Easy

Few desserts bring instant nostalgia quite like pineapple upside down cake. With its glossy caramelized fruit topping, bright cherries, and soft golden cake, it’s a timeless favorite that never goes out of style. Using a Duncan Hines cake mix makes this classic dessert wonderfully easy while still delivering that homemade taste everyone loves.

This cake is the perfect balance of sweet, buttery, and fruity. The brown sugar and butter melt together in the pan to create a rich caramel sauce that soaks into the pineapple as it bakes. When the cake is flipped, that sauce becomes a shiny topping that looks impressive with almost no effort. The pineapple rings stay juicy, the cherries add pops of color, and the cake underneath turns out soft and tender every time.

What makes this version especially appealing is how reliable it is. Duncan Hines cake mix provides a consistent, fluffy base that pairs beautifully with the caramelized topping. It’s ideal for potlucks, family dinners, holidays, or anytime you want a dessert that feels special without spending hours in the kitchen. Simple ingredients, classic flavors, and guaranteed smiles—this cake checks all the boxes.

Ingredients:

  • 1 box Duncan Hines yellow cake mix
  • Ingredients listed on cake mix box (usually eggs, oil, and liquid)
  • ½ cup unsalted butter
  • 1 cup packed brown sugar
  • 1 can (20 ounces) pineapple rings, juice reserved
  • Maraschino cherries
  • Optional: whipped cream or vanilla ice cream, for serving

Instructions:

  1. Preheat the oven to 350°F (175°C).
  2. Melt the butter and pour it evenly into the bottom of a 9×13-inch baking dish or round cake pan.
  3. Sprinkle the brown sugar evenly over the melted butter.
  4. Arrange pineapple rings over the brown sugar layer. Place a maraschino cherry in the center of each pineapple ring.
  5. Prepare the Duncan Hines cake mix according to the package directions, replacing some or all of the water with reserved pineapple juice for extra flavor.
  6. Carefully pour the cake batter over the pineapple layer, spreading gently to avoid disturbing the fruit.
  7. Bake for 40–45 minutes, or until a toothpick inserted into the center comes out clean.
  8. Remove the cake from the oven and let it cool for 5–10 minutes.
  9. Place a serving plate or cake stand over the pan and carefully invert the cake.
  10. Let the pan sit briefly before lifting it off to reveal the pineapple topping.
  11. Allow the cake to cool slightly before slicing and serving.

Duncan Hines Pineapple Upside Down Cake

A classic pineapple upside down cake made easy with Duncan Hines yellow cake mix and a caramelized pineapple topping.
Prep Time 10 minutes
Cook Time 45 minutes
Total Time 55 minutes
Servings: 12 slices
Course: Dessert
Cuisine: American
Calories: 360

Ingredients
  

Topping
  • 0.5 cup unsalted butter melted
  • 1 cup brown sugar packed
  • 20 oz pineapple rings juice reserved
  • maraschino cherries
Cake
  • 1 box Duncan Hines yellow cake mix
  • eggs as required on box
  • oil as required on box
  • pineapple juice used in place of water

Equipment

  • 9×13 baking dish or cake pan
  • Mixing bowl
  • Spatula
  • Oven

Method
 

  1. Pour melted butter into pan and sprinkle with brown sugar.
  2. Arrange pineapple rings and cherries over sugar.
  3. Prepare cake mix according to package directions.
  4. Pour batter over pineapple layer.
  5. Bake until golden and a toothpick comes out clean.
  6. Invert cake onto serving plate while warm.

Notes

Flip the cake while still warm to prevent sticking.

Tips & Tricks

  • Don’t let the cake cool too long before flipping or the topping may stick.
  • Use pineapple juice instead of water for enhanced flavor.
  • Place the cake pan on a baking sheet to catch any bubbling syrup.
  • Grease the sides of the pan lightly to help release the cake.

Variations

  • Use crushed pineapple for a more rustic topping.
  • Add chopped pecans or walnuts to the brown sugar layer.
  • Try a Duncan Hines butter golden or vanilla cake mix.
  • Add a splash of rum or vanilla to the batter for depth.

Serving Suggestions
Serve warm with whipped cream or a scoop of vanilla ice cream. This cake is also delicious at room temperature, making it perfect for parties and potlucks.

Storage Information
Store leftovers covered at room temperature for up to 2 days or in the refrigerator for up to 4 days. Reheat slices gently if desired.

FAQ

  • Can I use a different pan size? Yes, just adjust baking time as needed.
  • Why did my topping stick? The cake likely cooled too long before flipping.
  • Can I make this ahead? Yes, it tastes great the next day.

History / Fun Facts
Pineapple upside down cake became popular in the early 1900s when canned pineapple became widely available. Its iconic look and simple preparation made it a staple in American home baking—and it remains a beloved classic today.

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