Pineapple Upside-Down Layer Cake

Recipe By: Christina Tosi

Pineapple Upside-Down Layer Cake

This is not your grandma’s pineapple upside-down cake. Our PUD is a tropical-inspired dream with layers of fluffy coconut cake, tart poached pineapple, maraschino cherry soak, box cake mix inspired PUD frosting, and a yellow cake crumb topping.

This cake was originally created for a Milk Bar friend’s farewell as she headed to work in a tropical locale. We knew she loved making tiki-inspired beverages and was headed to a place where the sun always shines, so we created a PUD with a Milk Bar touch to sweetly send her off.

There are a lot of components to this cake, and this baking adventure is not for the faint of heart. But make it through and everyone will stand in awe of your incredible layer cake skills. We believe in you.

DECORATING TIP: Add a dash of tiki-flair by topping your pineapple masterpiece with a couple of cocktail umbrellas.

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Pineapple Upside-Down Layer Cake

Coconut Cake


Heat the oven to 350°F. Pan-spray a quarter-sheet pan and line it with parchment paper, or just line it with a silicone baking mat.


Combine the butter and both sugars in the bowl of a stand mixer fitted with the paddle attachment and cream together on medium-high for 2 to 3 minutes, until light and fluffy. Scrape down the sides of the bowl halfway through this process, and again at the end of it.


Add the eggs, one at a time, beating on medium-high for 1 minute after each addition. After you add the last egg, scrape down the sides of the bowl, then beat on high for 4 more minutes. Scrape down the sides of the bowl again.


Combine the buttermilk, oil, and vanilla extract and with the mixer on medium speed, stream them into the cake batter very slowly. It should take you approximately 3 minutes to add these liquids. Scrape down the sides of the bowl, increase the mixer speed to medium-high, and paddle for an additional 2 to 3 minutes, until the mixture is practically white, twice the size of your original fluffy butter-and-sugar mixture, and completely homogeneous. Don’t rush the process. You’re basically forcing too much liquid into an already fatty mixture that doesn’t want to make room for that liquid. There should be no streaks of fat or liquid. Stop the mixer and scrape down the sides of the bowl.


Whisk together the cake flour, baking powder, and salt in a medium bowl.


With the mixer on very low speed, slowly add the dry ingredients and mix for 45 to 60 seconds, just until your batter comes together. Scrape down the sides of the bowl, then mix on low for an additional 45 seconds to make sure no lumps of cake flour get left behind.


Add the coconut and mix until just combined.


Pour the cake batter into the sheet pan and, using a spatula, spread the batter in an even layer in the pan.


Bake for 30 to 35 minutes, rotating the pan front to back halfway through baking. The cake will rise and puff, doubling in size, but will remain slightly buttery and dense. At 30 minutes, gently poke the edge of the cake with your finger: the cake should bounce back slightly and the center should no longer be jiggly. If it doesn’t pass these tests, leave the cake in the oven for an additional 3 to 5 minutes.


Let the cake cool in the pan on a wire rack or, in a pinch, in the fridge or freezer (don’t worry, it’s not cheating). The cooled cake can be stored in the fridge, wrapped in plastic wrap, for up to 5 days.


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