Crushed Pineapple Upside Down Cake

My Pineapple Upside Down Cake recipe yields a sweet, moist, fluffy cake loaded with pineapple flavor! The cake isn't overly sweet or dense but the perfect bite every time.

If you're looking for other great desserts to bring to the cookout, consider these: Peanut Butter Cookies, Blueberry Basil Ice Cream, Cinnamon Rolls with Mascarpone Icing, Lemon Cupcakes, Chewy Dark Chocolate Chip Cookies, or Pineapple Upside Down Sticky Buns. 

This recipe will put any cake mix recipe with pineapple juice to shame. If you don't believe it, the recipe below will prove it.

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Where Did Pineapple Upside Cake Originate?

Canned pineapples became widely available in the US during the 1920s. In 1925, the Dole pineapple company held a recipe competition, which Mrs. Robert Davis from Norfolk, Virginia, won with her recipe for a pineapple upside-down cake. This led to the dessert's increased popularity in America.

The competition promised a cash prize of $50 for each of the 100 best recipes. Initially, the classic recipe was often baked in cast iron skillets or on top of the stove. Occasionally crushed pineapples were used instead of sliced pineapple.

Pineapple Upside Down Cake Ingredients

To make a delicious pineapple upside down cake, you'll need two sets of ingredients: one for the caramel pineapple sauce and one for the yellow cake. The cake itself will be buttery and tender, with the added sweetness and tanginess of pineapple.

Pineapple

I will use fresh pineapple over canned when possible, but crushed pineapples will work great too. When I use fresh, I finely chop the pineapples so there are pineapples in every bite.

Butter

You'll need a couple of sticks of unsalted butter for the sauce and the cake.

Brown Sugar

I prefer Imperial Sugar brown sugar and granulated sugar when baking because they have maintained the same quality for the past century and are Non-GMO certified. This assures me of their quality from the ground to my kitchen.

Cherries

I love using Luxardo maraschino cherries. The added depth of flavor from soaking in the cherry syrup is a real treat. You can usually find them near the cocktail garnishes.

Flour

You'll need a couple of cups of unbleached all-purpose flour, and you'll also need baking powder and salt.

All-Spice

This is the secret ingredient that separates my recipe from all others.

Eggs

You'll need 4 large eggs.

Evaporated Milk

Since evaporated milk is cooked, it provides an added layer of flavor.

Vanilla

A splash of pure vanilla extract goes into the caramel and cake.

How to Make Pineapple Upside Down Cake Recipe

I will teach you to make one of the best pineapple upside down cake recipes you've ever tasted.

Caramel Pineapple Sauce

First things first, preheat oven to 400°F. Then chop your pineapple to a small dice or use crushed pineapples.

Melt butter, brown sugar, vanilla, and kosher salt, in a 12-inch cast iron skillet over medium-high heat once the butter and sugar have melted. Sprinkle pineapples and cherries in the pan, and try to place the cherry in the center of each pineapple. 

You can use pineapple rings to give it a classic look.

Yellow Cake

We're going to use the reverse creaming technique for this yellow cake. Instead of creaming butter and sugar, combine the flour and butter, similar to a biscuit recipe. 

The reverse creaming produces a lighter and more tender cake.

Combine flour, sugar, baking powder, allspice, and kosher salt in a large bowl. Smash in softened butter with a fork or pastry cutter, then mix with a hand mixer until the flour mixture looks crumbly, about 3 minutes. Add eggs one at a time; the batter will be a thick batter. Then add milk and vanilla until the cake batter is smooth and thick. 

Pour cake batter into the cast iron skillet and bake for 35 minutes, rotating halfway; the cake is finished when a toothpick inserted in the center comes out clean; cool for 10-15 minutes.

Place a serving platter or cake plate on top of the skillet and turn over to release the cake. Serve warm with whipped cream or vanilla ice cream.

How To Store Upside Down Pineapple Cake?

Pineapple upside down cake is best eaten the same day but will remain fresh for 5 days in the fridge.
 
You could freeze the cake by placing them in a freezer-safe storage bag for 2 months. 
 
Reheat the cake in the microwave for 10-15 seconds. 

Pro Recipe Tips & Tricks

Here are the best practices, techniques, substitutes, and flavor builders you'll need for a succulent upside down cake pineapple recipe.

• How to cut a pineapple. Cut in slices and use a cookie cutter to remove the core, or cut pineapple strips by cutting around the core.
• Drain on a paper towel using canned crushed pineapples, rings, tidbits, or chunks.
• You don't have to finely chop your pineapples. You can use pineapple slices.
• Feel free to use self-rising flour instead of unbleached flour. Omit the baking powder and salt.
• You can make a gluten-free pineapple upside down cake by swapping the flour for gluten-free flour.
• You can use cake flour for a 1:1 swap of all-purpose flour.
• Check the expiration date on your baking powder. Older baking powder may keep your delicious cake from rising.
• You can use classic maraschino cherries if you cannot find the Luxardo kind.
• Feel free to use any milk you have on hand.
• You can use a 9 x 13 baking pan or a large round cake pan to bake the cake.
• You can use light brown sugar in the cake, too, instead of using granulated sugar.
• Feel free to use dark brown sugar instead of light brown sugar.
• Cinnamon is an excellent substitute for all-spice.

FAQs

Here are the top questions readers have about making a homemade pineapple upside down cake from scratch.

Why is my pineapple upside down cake soggy?

Your pineapple upside down cake might be soggy due to too much topping, undercooked batter, improper cooling, or improper storage.

Too much butter in the caramel mixture can cause the cake to become overly moist. Another reason could be that you didn't cook the cake long enough; check for doneness before removing it from the oven. Lastly, it could be that you used more pineapple than necessary; too much pineapple can make it soggy.

Can I use pineapple juice instead of water in a cake mix?

Yes, you can use pineapple juice instead of water in a cake mix to add more pineapple flavor to your cake.

Do you eat pineapple upside down cake warm or cold?

Depending on your preference or the occasion, you can serve pineapple upside down cake, either warm or cold.

Why is my pineapple upside down cake not rising?

The reason your pineapple upside down cake may not be rising could be due to excessive fruit or sugar making the batter heavy or the inaccurate measurement of baking powder. Also, make sure that you're using the freshest baking powder possible.

What is the trick to flipping pineapple upside down cake?

To successfully flip an upside-down pineapple cake without falling apart, let it cool in the pan for 5-10 minutes. Then, run a knife along the edges of the pan and place a serving plate on top. Confidently flip the pan over to release the cake onto the plate.

Is it better to make a pineapple upside down cake the day before?

Pineapple upside down cake can be made a day ahead, allowing the flavors to meld and the cake to become more moist and flavorful.

Do you have to refrigerate pineapple upside down cake after baking?

It would be best to refrigerate the pineapple upside down cake after baking to prevent the fruit from spoiling and keep it fresh for longer.

Should you use parchment paper when baking a pineapple upside down cake?

It's unnecessary, but using parchment paper when baking pineapple upside down cake can prevent sticking and keep it intact when flipping it over.

Should I flip the cake and put it in the fridge or just put it in the fridge?

Flipping the pineapple upside-down cake and then putting it in the fridge to prevent the fruit from getting soggy is better. The longer you wait to flip the cake, the greater the chance of the cake sticking as the caramel sauce cools.

How long do you let a cake cool before inverting it?

Let your cake cool in the pan for 10-15 minutes before inverting it and letting it cool completely on a wire rack.

Can pineapple upside down cake be made with fresh pineapple?

Absolutely, pineapple upside down cake can be made with fresh pineapple.

Can you freeze pineapple upside down cake?

Wrap the pineapple upside down cake slices in plastic wrap, then place them in a freezer-safe storage bag for 2 months.

Is pineapple upside down cake Hawaiian?

Pineapple upside down cakes did not originate in Hawaii; they became popular in the United States during the 1920s when canned pineapple was introduced.

Is pineapple upside down cake Southern?

Pineapple upside down cakes has been associated with Southern cuisine in the United States since the 1920s, when the winner of a recipe competition held by the Dole pineapple company came from Norfolk, Virginia.

More Dessert Recipes

If you love sweet potatoes as much as I do, you'll love these recipes too!

• Monkey Bread
• Carrot Walnut Cake
• New Orleans Bread Pudding with Bourbon Sauce
• Chocolate Banana Pudding
• Butter Rum Cake
• Fudge Brownie Ice Cream

Before You Begin

Here are my steps for getting organized and moving fast in the kitchen.

Step 1: Preheat oven to 400°F before pulling the ingredients out.

Step 2: Put everything measured into individual bowls.

Step 3: Make sure your oven is heating correctly to 400°F; we don't want any surprises.

Step 4: Start following the recipe and get ready for the best pineapple upside down cake you've ever enjoyed.

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📖 Recipe

Crushed Pineapple Upside Down Cake

Kenneth Temple

My Pineapple Upside Down Cake yields a sweet, moist, fluffy cake loaded with pineapple flavor! Each slice has the perfect bite every time.

5 from 5 votes

Print Recipe Pin Recipe

Prep Time 15 minutes mins

Cook Time 35 minutes mins

Cooling 15 minutes mins

Total Time 1 hour hr 5 minutes mins

Course Brunch, Dessert

Cuisine Southern

Servings 15 persons

Calories 297 kcal

Ingredients

  

1x2x3x

Caramel Pineapple Sauce:

• 2 ½ cups chopped ripe pineapple or 1 20 can of crushed pineapples, drained
• 6 tablespoons unsalted butter sliced
• 1 cup Imperial Sugar light brown sugar
• 2 teaspoons vanilla extract
• ¼ teaspoon kosher salt
• 12-24 cocktail maraschino cherries preferably Luxardo

Yellow Cake:

• 2 cups unbleached all-purpose flour
• 1 ¼ cup Imperial Sugar granulated sugar
• 1 tablespoon baking powder
• 1 teaspoon all spice
• ½ teaspoon kosher salt
• 1 stick unsalted butter softened
• 4 large eggs room temperature
• 1 ½ cups evaporated milk
• 2 teaspoons vanilla extract

Instructions

 

Caramel Pineapple Sauce

• Preheat oven to 400°F. In a 12-inch cast iron skillet over medium-high heat, melt butter then stir in brown sugar, vanilla and salt, until sugar has melted. Sprinkle pineapples and cherries in the pan.

Yellow Cake

• In a large mixing bowl combine flour, sugar, baking powder, all spice, and salt. Smash in butter, then mix with a hand mixer until texture looks crumbly about 3 minutes. Add eggs one at a time, batter will look like thick cake batter. Then add milk and vanilla, until cake batter is smooth and thick.
• Pour cake batter into the skillet and bake for 35 minutes, rotating halfway, cool for 15 minutes. Place a platter or plate on top of the skillet and turn over to release cake. Cool for 15 minutes before serving with whipped cream or vanilla ice cream.

Video

Notes

Pro Recipe Tips & Tricks

Here are the best practices, techniques, substitutes, and flavor builders you'll need for a succulent upside down cake pineapple recipe.

• How to cut a pineapple. Cut in slices and use a cookie cutter to remove the core, or cut pineapple strips by cutting around the core.
• Drain on a paper towel using canned crushed pineapples, rings, tidbits, or chunks.
• You don't have to finely chop your pineapples. You can use pineapple slices.
• Feel free to use self-rising flour instead of unbleached flour. Omit the baking powder and salt.
• You can make a gluten-free pineapple upside down cake by swapping the flour for gluten-free flour.
• You can use cake flour for a 1:1 swap of all-purpose flour.
• Check the expiration date on your baking powder. Older baking powder may keep your delicious cake from rising.
• You can use classic maraschino cherries if you cannot find the Luxardo kind.
• Feel free to use any milk you have on hand.
• You can use a 9 x 13 baking pan or a large round cake pan to bake the cake.
• You can use light brown sugar in the cake, too, instead of using granulated sugar.
• Feel free to use dark brown sugar instead of light brown sugar.
• Cinnamon is an excellent substitute for all-spice.

Storage:

Pineapple upside down cake is best eaten the same day but will remain fresh for 5 days in the fridge.

You could freeze the cake by placing them in a freezer-safe storage bag for 2 months. 

Reheat the cake in the microwave for 10-15 seconds. 

Nutrition

Calories: 297kcalCarbohydrates: 52gProtein: 5gFat: 8gSaturated Fat: 4gPolyunsaturated Fat: 1gMonounsaturated Fat: 2gTrans Fat: 0.2gCholesterol: 63mgSodium: 251mgPotassium: 169mgFiber: 1gSugar: 38gVitamin A: 286IUVitamin C: 14mgCalcium: 145mgIron: 1mg

Keyword pineapple upside down cake, pineapple upside down cake recipe, crushed pineapple upside down cake, crushed pineapple upside down cake recipe

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