We Made the Iconic Duncan Hines Double-Layer Pineapple Upside-Down Cake and It’s a Tropical Delight

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The classic pineapple upside-down cake has been a go-to dessert for decades. But the Duncan Hines double-layer pineapple upside down-cake takes this tropical treat to the next level!

Does it get more retro than a pineapple upside-down cake? This beauty immediately conjures up visions of ’50s and ’60s kitsch, but the recipe has been around for close to 100 years now. Though usually a one-layer cake, this Duncan Hines double-layer pineapple upside-down cake is twice as nice! The same delectable flavors that made this a favorite for so long have been transformed into a darling layer cake with a creamy frosting center and cherries on top.

How could I resist? I decided it was time to make this pineapple confection!

Duncan Hines Double-Layer Pineapple Upside-Down Cake

Duncan Hines Pineapple Cake IngredientsNancy Mock for Taste of Home

Ingredients

  • Nonstick spray
  • 1/2 cup unsalted butter, melted
  • 1 cup light brown sugar, firmly packed
  • 1 can (20 ounces) pineapple rings, drained
  • 14 maraschino cherries, drained
  • 1 package (15.25 ounces) Duncan Hines Signature Pineapple Supreme Cake Mix
  • 1 cup water
  • 3 eggs
  • 1/2 cup vegetable oil
  • 3/4 cup heavy whipping cream
  • 1/4 cup coconut rum (like Malibu)
  • 1/3 cup Easy Vanilla Buttercream Frosting or Duncan Hines Classic Creamy Vanilla Frosting

Nancy’s Tip: The coconut rum liquor is optional, and the cake will still be delicious if you decide to omit it.

Tools You’ll Need

Nancy’s Tip: If you don’t have 8-inch round cake pans, larger round pans can be used. Just keep in mind your cake layers will be thinner and need slightly less baking time.

Getting Started

Duncan Hines Pineapple Cake Getting StartedNancy Mock for Taste of Home

To make sure the cakes released cleanly, I cut parchment paper circles to place in the bottom of the 8-inch cake pans, followed by a coating of baking spray. Then, I poured in the melted butter followed by a generous layer of brown sugar. (What a tasty start to this cake!) Then, four pineapple rings are laid in an even layer in each pan. Half of a maraschino cherry goes into the center of each pineapple ring.

Next, the Pineapple Supreme cake mix is quickly blended with water, eggs and oil to make a smooth batter. I divided the batter between the two pans, pouring it carefully over the pineapples and cherries. Then into the oven they went!

The cake layers only took about a half hour to bake, and it wasn’t long before a sweet pineapple scent filled the kitchen.

Making the Filling and Frosting

Duncan Hines Pineapple Cake FrostingNancy Mock for Taste of Home

The filling for the center of this cake and to decorate the top is not the usual frosting found on other layer cakes. Instead, the recipe calls for the heavy cream to be mixed at high speed with a hand mixer until it turns into unsweetened whipped cream. Next, a small amount of vanilla frosting gets folded into the whipped cream.

I used a simple homemade vanilla buttercream (though the recipe calls for Duncan Hines Classic Vanilla Frosting). When I tasted this filling, I was surprised at how delicate the sweetness was, especially compared to super-sweet buttercream frostings typically used on cakes. I was a little worried that it wouldn’t be sweet enough in the final dessert.

Assembling the Cake

Duncan Hines Pineapple Cake AssemblyNancy Mock for Taste of Home

I turned the baked cake layers out of the pans and was pleased to see that the parchment paper did the trick! The pineapple rings and cherries were baked perfectly into the cake with no bits sticking to the pan. Once the cake layers were completely cool, I flipped them back over. The cakes had come out with a slight dome that would have made for uneven layers, so I used a serrated knife to slice the domes away and make the cake layers flat.

It was finally time to assemble the cake! This began with one cake layer on a cake board, with the pineapple and cherry side facing up. My twist on the original recipe is to add an extra layer of flavor… in the form of Malibu rum! I used a pastry brush to spread the top of the cake with the liquor.

Next, I spread about 2/3 of the whipped cream-frosting mixture over the cake, right up to the edge. The second cake layer came next, again with the fruit facing up. I gave it a gentle press to help make that layer of frosting peek out. This cake layer also got a light brushing of coconut rum. Then I topped each pineapple ring with a mound of whipped cream frosting. The final touch was adding a whole maraschino cherry with the stem still attached to each frosting mound.

What a lovely and cheery cake!

The Taste Test

Slice Of Duncan Hines Pineapple CakeNancy Mock for Taste of Home

My family and I couldn’t wait to dig into thick slices of this dessert—it was our first time trying a pineapple upside-down cake of any kind! The first thing that struck us was how moist the cake is, and each bite was full of lovely pineapple flavor. The top of each cake layer has a sinfully delicious layer of caramelized brown sugar that surrounds the tender rings of pineapple. The fruit and cake get a light flavor from that coconut rum, too.

And that whipped cream frosting that I was worried about? As it turns out, the lightly sweet frosting is a nice balance with the sweetness of the cake and fruit. I could see how a sweeter, more traditional frosting would make the whole cake feel heavy and overly sugary. The whipped cream-style filling is much better suited to this pineapple cake.

Perhaps the biggest surprise was that we found this cake to be even more delicious cold. Cake slices eaten straight from the fridge are very moist and the flavors seem more concentrated, more intense!

I wasn’t sure what to expect when I began making this cake, if it would be a one-time adventure or live up to the hype and become a new favorite. Given how quickly this whole cake disappeared, I can safely say that pineapple upside-down cake will be back again soon, and definitely with that light frosting and splash of coconut rum.

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Nancy Mock
Discovering restaurants, tasting bakery treats, finding inspiration in new flavors and regional specialties—no wonder Nancy loves being a food and travel writer. She and her family live in Vermont and enjoy all things food, as well as the beautiful outdoors, game nights, Avengers movies and plenty of maple syrup. Find Nancy’s writing and recipes at her website: Hungry Enough To Eat Six.