{Triple Layer} Pineapple Upside-Down Cake

{Triple Layer} Pineapple Upside-Down Cake: This pineapple upside down cake is three layers of caramelized pineapples, maraschino cherries, and homemade cinnamon whipped cream! This layered twist on the classic pineapple upside-down cake recipe is sure to be a family favorite!

This is our favorite recipe for the Best Pineapple Upside Down Cake! Don’t let the multiple layers and homemade whipped cream fool you — this is an Easy Pineapple Upside Down Cake Recipe!

I’m out of control.

Well, in the cake department, at least.

Coconut Cake.

Chocolate Peanut Butter Oreo Cake.

Lemon Coconut Cake.

Vanilla Cake with Strawberry Buttercream.

Aaaaaand there are two more cupcake recipes in the works.

It’s becoming a problem.

In my defense, this very large, very tasty, monstrosity of a cake was made for my dad for Father’s Day.

Of course, I’m obnoxious and couldn’t leave well enough alone, and decided that three layers were far better than one layer.

Yeah.

Like I said, I’m out of control.

But, triple the layers means triple the fruit, right? Aka triple the nutrients?

I mean, it makes sense. And it totally justifies us being able to have our cake and eat it too!

(Plus, if you’re already making one layer, why not just make three?? It’s easy–I promise!!)

Pineapple Upside Down Cake From Scratch: 

So, let’s get down to the nitty gritty of this tower of a cake.

Preheat the oven to 350. With a mixer, cream together butter and oil. Add in white and brown sugar, mixing until combined. Add in eggs, one at a time, stirring until just combined.

In a separate bowl, sift together, flour, corn starch, baking powder and salt.

In a liquid measuring cup, whisk together milk, pineapple juice, Greek yogurt, and vanilla extract. Alternately add in the dry ingredients and the wet ingredients into the butter batter, beginning and ending with the dry ingredients.

Add melted butter to each cake pan and sprinkle with brown sugar. Place 7 pineapple rings in each cake pan. Cut maraschino cherries in half, and place two, uncut side down, in each pineapple hole. Spread crushed pineapple over the pineapple and cherries, in order to fill all the areas with pineapple.

Divide the batter between the three cake pans, and bake for 30 minutes, or until a cake tester comes out clean.

Homemade Pineapple Upside Down Cake Tips & Tricks:

• Due to all of the caramelized goodness, pineapple upside down cakes can be slightly fragile. Be extra careful when handling the cakes, because they can crack easily.
• The corn starch in this recipe makes the cakes extra tender. Cornstarch + all purpose flour = homemade cake flour.
• I cut the maraschino cherries in half, but you can add them in whole.
• The cake should be refrigerated until you are ready to serve.
• The butter and oil combination yields for a super moist cake, and makes, in my opinion, for an award winning Pineapple Upside Down Cake!

Be still my pineapple lovin’ heart.

5 from 3 votes

{Triple Layer} Pineapple Upside-Down Cake

Prep: 45 minutes mins

Cook: 30 minutes mins

Total: 1 hour hr 15 minutes mins

This pineapple upside down cake is three layers of caramelized pineapples, maraschino cherries, and homemade cinnamon whipped cream! This layered twist on the classic pineapple upside-down cake recipe is sure to be a family favorite!

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Ingredients

 

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Pineapple Topping

• ▢ 3 20 oz cans pineapple rings (in pineapple juice or fresh); drained (save 1/4 cup of juice for the cake)
• ▢ 1 20 oz can crushed pineapple (in pineapple juice or fresh); drained
• ▢ 14 maraschino cherries, cut in half
• ▢ 6 Tbsp butter, melted
• ▢ 3/4 cup brown sugar

Cake

• ▢ 1/2 cup butter, softened
• ▢ 1/3 cup vegetable oil
• ▢ 3/4 cup brown sugar
• ▢ 3/4 cup white sugar
• ▢ 4 large eggs
• ▢ 2 2/3 cups all purpose flour
• ▢ 1/3 cup corn starch
• ▢ 2 1/2 tsp baking powder
• ▢ 1/2 tsp salt
• ▢ 3/4 cup milk
• ▢ 1/4 cup pineapple juice, drained from can is fine
• ▢ 3 tsp vanilla extract
• ▢ 1/4 cup Greek Yogurt

Whipped Cream

• ▢ Cinnamon Whipped Cream (recipe linked below)

Instructions

 

• Preheat oven to 350 degrees and grease 3 cake pans ( 9" cake pans) with cooking spray (just to ensure the cakes do not stick).

Pineapple Topping

• Place 2 Tbsp of melted butter in each cake pan, and tilt the cake pan around until the better has spread a bit. Sprinkle 1/4 cup brown sugar in each pan.
• Arrange pineapple rings in each pan (7 rings should fit nicely in each pan). To fill in any gaps on the outer edge, slice any leftover pineapple rings into cubes and add them between the rings. Place two cherry halves in the center of each pineapple ring, making sure the uncut side is facing downwards (that way the pretty side will show when the cake is out of the pan). Lastly, spread about 1/4 cup of crushed pineapple over the pineapple rings in order to fill in all areas with pineapple. Set aside.

Cake

• With a mixer, beat butter until light and fluffy, about 1-2 minutes. Add in oil and mix until combined. Add in both brown sugar and white sugar, beating until well combined (scrape the sides of the bowl with a rubber spatula if needed). Add in the eggs, one at a time, beating until just combined.
• In a separate bowl, sift together flour, corn starch, baking powder, and salt.
• Whisk together milk, pineapple juice, vanilla extract and Greek yogurt.
• Alternately add the dry ingredients and the wet ingredients into the butter mixture, beginning and ending with the dry ingredients. Mix until just combined.
• Divide batter evenly between the three cake pans. Bake for 30-35 minutes (mine was done right at 30 minutes), or until a cake tester comes out clean.
• Allow cakes to cool completely.

Whipped Cream

• Once your cakes have cooled, make the Cinnamon Whipped Cream. Set aside 1/2 cup of whipped cream for decorating.
• Place the bottom cake layer on a cake stand and spread about half of the remaining whipped cream over the cake, keeping the whipped cream about 1/2" in from the edge of the cake (as the layers are stacked on top, the whipped cream will spread to the edge). Place the middle layer on top, and spread with remaining whipped cream. Add the top layer, and with a piping bag and star tip, pipe on the whipped cream. Top with a cherry, if desired.
• Cake must be kept in the refrigerator until you are ready to eat.
• Enjoy!

Notes

Cinnamon Whipped Cream

The nutrition facts provided are calculated using a third-party tool and are estimates only. Actual nutritional content may vary based on the ingredients and brands you use, as well as portion sizes. For accurate results, please consult a registered dietitian or nutritionist.

Course Dessert

Cuisine American

Make sure to tag me on Instagram and leave a rating below and let me know how it turned out!

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{No Bake} Tropical Cream Pie

Double Chocolate Cupcakes

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