A Classic Pineapple Upside Down Cake with a Secret Ingredient

Let’s put a playful spin on pineapple upside down cake with a surprising secret ingredient that makes each bite extra moist and tender—Duke’s Mayo! Don’t worry; you won’t taste it, but it brings a bakery-quality richness that’ll keep everyone guessing.

Friends, I’d tell you to buckle up, but you know how we do around here.  You know we like to sneak mayonnaise into our best cake recipes (see: Classic Hummingbird Cake made with Duke’s Mayo). It sounds strange, but I feel like you’ve come to trust me on this one!

This week we’re talking about the classic Pineapple Upside Down Cake—the one with a caramelized pineapple layer and a literal cherry on top.  The mayo (you know it’s Duke’s or bust) is our secret weapon for the fluffiest, moistest vanilla cake. Mayo might seem like an oddball here, but think about it: it’s eggs and oil (and that hint of vinegar twang), which are already cake essentials.  With this cake, mayo is whipped into the butter and sugar, creating the fluffiest, richest batters.

In a few weeks, when my whole family crowds into the house for Thanksgiving week, this pineapple cake is going straight onto the morning snack table, and I fully expect it to disappear faster than anything. Trust me, it’s worth the raised eyebrows; I’m sure they’ll be sold after one bite.

Ok let’s bake!

Here are the ingredients you’ll  need to make this pretty perfect Pineapple Upside Down Cake:

•  all-purpose flour

•  baking soda, baking powder, and kosher salt for a tender cake crumb and and flavor balance

•  unsalted butter

•  granulated sugar

•  large eggs

•  whole milk

•  almond extract if you love that wedding cake flavor as much as I do.

•  crushed pineapple

•  and the secret ingredient Duke’s Mayo to bring its signature twang to the cake along with helping create an extra tender crumb and fluffy cake.

• marachino cherries

• sweetened whipped cream

This is easily one of my favorite simple and fool-proof cake batters.  It starts where many great cakes start, by creaming together butter and sugar.

Beat the butter and sugar until well combined, then add Duke’s Mayo and whip the mixture until pale and fluffy, which is a sign that the fats are well aerated and going to bake into a very light cake.

Beat in the eggs, one at a time, will further ensure that the cake has a sturdy but light crumb. We want a little cake cloud for our pineapple layer and this is just the ticket!

PRO TIP for the perfect pineapple layer:

Simmer the canned crushed pineapple, and the sugar, in a medium saucepan before adding a slurry of cornstarch and water to the bubbling fruit.  The cornstarch will thicken the sweetened pineapple juices making for a firm and flavorful pineapple layer that won’t make the bottom turned top of your cake soggy!

Note:  We tested this cake recipe with canned pineapple rings that we “crushed” in a food processor and had trouble getting the cake to release from the pan without leaving some of the precious pineapple behind.  There’s something magical (and specific) about canned crushed pineapple for this recipe!

Bake until the cake is baked through and golden brown across the top. Insert a toothpick or cake skewer into the center of the cake to test for doneness.  If the pick emerges with a few moist crumbs, great! If you see wet batter on the pick, give the cake more time in the oven.

Allow the cake to cool for 15-20 minutes on the counter.  To release the cake, run a butterknife around the edge of the cake to release any sticky bits from the sides.  Place a plate on top of the cake pan, off a small prayer up the the baking goddesses and invert the cake pan.  The entire pineapple layer and cake should release from the pan.

Once the cake has cooled, pipe with sweetened cream and dot with a marachino cherry.

It’s perfect, really! This classic cake slice is a perfect breakfast cake, in my opinion.  I also love it with an afternoon coffee and would never turn up my nose at a warm slice after dinner.

The pineapple caramelizes to a beautiful jammy consistency. The cake is so pillowy thanks to the Duke’s Mayo, with just the right amount of sweetness and almond scent.  This is a MUST BAKE, friends!

Leave any recipe questions or comments below! If you bake this cake, please come back and rate the recipe! It helps the next baker who comes along feel confident in their bake.

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A Classic Pineapple Upside Down Cake with a Secret Ingredient

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  • Author: Joy the Baker adapted from Karlee Flores

Ingredients

Scale

For the pineapple layer:

  • 120 ounce can crushed pineapple
  • 2 tablespoons lightly packed light brown sugar
  • 1 tablespoon lemon juice
  • 3 tablespoons cornstarch + 3 tablespoons water

For the yellow cake:

  •  2 cups (240 grams) all-purpose flour
  • ½ teaspoon baking soda
  • 1/2 teaspoon baking powder
  • ½ teaspoon kosher salt
  • 1/2 cup (113 grams) unsalted butter, room temperature
  • 2/3 cup (170 grams) granulated sugar
  • 1/2 cup Duke’s mayonnaise
  • 1/2 teaspoon almond extract
  • 2 large eggs, room temperature
  • 1/3 cup (75 grams) whole milk

For garnish:

  • Sweetened whipped cream and a star piping tip
  • Maraschino cherries

Instructions

  1. Place a rack in the upper third of the oven and preheat the oven to 350 degrees F. Grease a 9-inch cake pan with nonstick cooking spray, line the bottom with parchment paper and set aside.
  2. Pour the crushed pineapple, sugar and lemon juice in a medium saucepan and place over medium heat mixing occasionally. In a small bowl, mix the cornstarch with 3 tablespoons of cold water. Mix until there are no more lumps.
  3. Once the pineapple is simmering, slowly pour in the cornstarch slurry while mixing constantly with a rubber spatula. Continue to stir until the mixture thickens, about 2 minutes. Pour into the prepared cake pan and smooth out into an even layer. Let the mixture cool while making the cake layer.
  4. In a medium bowl, whisk the flour, baking soda and salt. Set aside.
  5. In a standing mixer with a paddle attachment, beat the butter and sugar together just until combined. Stop the mixer and scrape down the sides of the bowl. Add the mayonnaise and almond extract. Turn the mixer to medium speed and let whip for about 5 minutes until the mixture fluffs and turns pale in color. Scrape down the sides of the bowl.
  6. Add the eggs, one at a time and mix for about 30 seconds each. Add half of the flour mixture and beat just until combined. With the mixer on low, slowly add the milk. Add the rest of the flour mixture and beat on high for another 30 seconds. Scrape down the mixing bowl with a rubber spatula and mix out any uneven batter.
  7. Pour on top of the slightly cooled pineapple mixture and spread evenly with an offset spatula. Lightly tap on the counter a few times to remove any air bubbles.
  8. Place into the preheated oven to bake for 28-32 minutes, or until the middle of the cake has set. Remove from the oven and let cool on the counter for about 15-20 minutes.
  9. Run a knife around the sides of the cake. Turn out onto a plate and remove the parchment paper. Let cool another 15 minutes before covering with plastic wrap and placing in the fridge to cool for at least 2 hours.
  10. To serve, top with whipped cream and a garnish of maraschino cherries.

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