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Homemade Pineapple Upside Down Cake

Imagine a cake that is old-fashioned and reminiscent of a time when things were simpler. A cake that has a beautiful caramelized top and sweet pineapple flavor. We’re talking about old-fashioned pineapple upside down cake. This vintage treat is still as delicious today as it was decades ago. So, if you’re looking for a unique dessert to wow your guests, look no further than this retro classic!

Pineapple cake on a white plate. Homemade Pineapple Upside Down Cake is a delicious and refreshing cake.

Prep Time: 20 minutes
Cook Time: 40-45 minutes
Total Time: 60 minutes
Servings: 9
Preparation Level: Easy
Yield: 1 (8×8-inch pan)

What I Love About This Classic Dessert

Pineapple upside-down cake is a classic recipe, and this stays true to that vintage flavor, method, and style. It’s a clear and easy recipe to follow. You can recreate the moist cake with pineapple flavor and a caramelized top. And I will share how to make the recipe with canned or fresh pineapple.

Ingredients

Topping

  • 1/4 cup of butter, melted
  • 1/2 cup of brown sugar
  • 20-ounce can of pineapple slices (or fresh pineapple)
  • Handful of pitted maraschino cherries

Cake

  • 1/2 cup of butter softened
  • 3/4 cup of granulated sugar
  • 2 eggs
  • 1 teaspoon of vanilla extract
  • 1-1/2 cups of all-purpose flour sifted
  • 1-1/2 teaspoons of baking powder
  • 1/4 teaspoon of salt
  • 1/2 cup of milk

A full printable recipe with measurements and instructions is listed at the bottom of the post on the recipe card.

Taking a bite out of cake

How To Make Pineapple Upside Down Cake

Topping

Spray an 8-inch by 8-inch baking dish with nonstick cooking spray. Add the brown sugar to the greased baking dish. The sugar will create a brown sugar glaze on the top of the cake after baking. Pour the melted butter over the brown sugar and mix it all together. Spread the butter and sugar mixture over the bottom of the dish.

Next, lay the pineapple slices on top of the brown sugar and butter mixture. Place the cherries in the little spaces in between. You can add as many cherries as you’d like. Typically, you add more pineapples, but mine was small, so I only had a few slices. 

Making the Cake

Add the softened butter to a large mixing bowl and cream for about one minute. Add the sugar and cream for about one more minute. Plop in the eggs, one at a time, and mix them into the batter. Next, add the vanilla extract. Then, measure out your baking powder and prepare it to add to the flour. 

Next, add the flour, salt, and baking powder to a sifter. Sift the ingredients into the bowl. Sifting the flour will add a light, fluffy texture to your cake. Mix the flour mixture into the batter. Pour the milk into the batter and mix together. 

Pour the batter on top of the pineapple and spread it out evenly. I baked it in my 8″ x 8″ dish. It did make it a thicker cake in the smaller dish, which was delish! 

Bake for approximately 40-45 minutes or until a cake tester comes out clean. If the cake is not done, extend the baking time for a few minutes at a time.

Homemade pineapple upside down cake made from scratch on white plates.

Allow the cake to cool, and invert it onto a plate or cookie sheet. It helps to scrape the sides with a knife before inverting so the cake doesn’t stick. 

Tips

  • Make sure you don’t over-mix the batter; otherwise, it might turn out dry and dense. You want it to be a moist cake. If your cake comes out dry, add a few tablespoons of the leftover pineapple juice to the batter.
  • Grease the pan well before adding the pineapple and cherries; otherwise, the cake might stick to the pan and not come out easily.
  • I used a ceramic baking dish, but you can also use a heavy skillet, such as a 10-inch cast-iron skillet, for the recipe. The cooking time is the same in a skillet or baking dish.
  • Use a cake tester to check the center of the cake for doneness. If it’s still a bit wet, bake it a few more minutes. If the top is getting a little bit brown you can place some aluminum foil over the top while it finishes baking.
  • Pineapple slices have a lot of juice, so you need to dry them off before adding them to the baking dish. Grab a paper towel and pat dry the slices to help dry them off a little. This will help keep your cake from getting too soggy.

Leftovers and Storage

You will need to regrigerate the cake, but make sure it is in an airtight container or covered with some plastic wrap. It is good for about three days and then the cake will start to get wet from the pineapple juice.

You can freeze an upside-down pineapple cake. Allow the cake to cool to room temperature, wrap it in plastic wrap, and store it in an airtight container. The cake can be frozen for up to three months. When you’re ready to serve it, place it in the refrigerator to thaw overnight. Having said that, it won’t taste as good as a freshly baked cake.

Substitutions and Variations

  • If you are using fresh pineapple, you will need about seven slices.
  • Swap out the pineapple for another fruit that is in season, such as peaches or pears.
  • Add some cinnamon and nutmeg to the topping for a more fall feel.
  • Using a yellow cake mix such as Betty Crocker can help you make the recipe faster.
A slice of cake on a white plate with a fork

Make Ahead or Not

You can make part of the cake ahead of time. Wait to add the brown sugar and pineapple layer until you are ready to bake the cake. You can mix the cake portioin a day ahead, but leave it in the mixing bowl and cover it with plastic wrap and keep it refrigerated. When you are ready to bake it, let the cake batter come to room temperature before addng to the baking dish.

More Delicious Pineapple Recipes

Pineapple upside down cake from scratch is an easy and delightful dessert.

Pineapple upside down cake is definitely a classic dessert that always impresses guests. It’s easy to make, so you can knock this one out of the park even if you’re not an experienced baker. Be sure to get the cake recipe, add a scoop of vanilla ice cream on the side, and give it a try! It might just become your favorite cake.

Homemade Pineapple Upside Down Cake is a delicious and easy recipe.

Homemade Pineapple Upside Down Cake

Yield: 9 pieces
Prep Time: 20 minutes
Cook Time: 40 minutes
Total Time: 1 hour

Who doesn’t love an old fashioned pineapple upside down cake? It is such a classic dessert that always seems to hit the spot. Plus, it is really easy to make – you just need a few simple ingredients that you probably already have in your kitchen. So why not give it a try today? You won’t be disappointed!

Ingredients

Topping

  • 1/4 cup butter, melted
  • 1/2 cup brown sugar
  • 20 ounce can pineapple slices (or fresh pineapple - you will need 7 slices)
  • Handful of pitted maraschino cherries

Cake

  • 1/2 cup butter, softened
  • 3/4 cup sugar
  • 2 eggs
  • 1 teaspoon vanilla extract
  • 1-1/2 cups all-purpose flour, sifted
  • 1-1/2 teaspoons baking powder
  • 1/4 teaspoon salt
  • 1/2 cup milk

Instructions

Preheat oven to 350-degrees.

Grease a 8-inch x 8-inch baking dish.

Topping

  1. Add the brown sugar to the bottom of the pan.
  2. Melt butter, pour over the top of the brown sugar, mix together, and spread over the entire dish.
  3. Place the pineapples and cherries on top of the brown sugar. (I like to place cherry in the center of each pineapple slice).

Cake

  1. Start by adding the butter to a large bowl and cream for one minute.
  2. Add the sugar and cream again for one more minute.
  3. Add the eggs, one at a time, and mix together.
  4. Add the vanilla and mix together.
  5. Combine flour, salt, and baking powder. Sift into the bowl and mix.
  6. Add the milk, mix together, and gently pour cake batter over pineapple.
  7. Bake for 40-45 minutes or until a cake tester comes out clean.
  8. Let cake cool to room temperature and turn cake upside down onto a cake plate.

Notes

I used an 8-inch by 8-inch baking dish for the recipe because my pineapple was small. If you use more pineapple, you can use a larger cake pan. However, your cake will not be as thick.

If you used canned pineapple, be sure to drain pineapple juice before removing the pineapple slices. Dry the pineapple slices with a paper towel before adding to the baking dish.

Nutrition Information:
Yield: 16 Serving Size: 1
Amount Per Serving: Calories: 356Total Fat: 10gSaturated Fat: 6gTrans Fat: 0gUnsaturated Fat: 3gCholesterol: 47mgSodium: 184mgCarbohydrates: 67gFiber: 5gSugar: 45gProtein: 4g

Nutrition is approximate.

Did you make this recipe?

Please leave a comment on the blog or share a photo on Pinterest

Growing Pineapples

Our old neighbor gave us the top of her pineapple a couple of years ago, and we grew a pineapple with it. It was easy, and all we had to do was wait about two years. Ha! I never knew, before growing this pineapple, that it took so long to grow them. Ours was small but as ripe and sweet as they get. 

As a kid, my husband asked his mom to make homemade pineapple upside down cake quite often, and he always loved it. So, he asked me to make one with our homegrown pineapple, and it turned out amazing. It’s such a happy cake!

Growing a pineapple in the backyard was easy.

Here’s the pineapple in the pot. It’s neat the way the pineapple grows out of the top of the leaves. Those are some sharp leaves, too. It might poke your eye out! 

Homemade pineapple upside down cake is a delicious dessert any time of year.

The pineapple didn’t grow too large, but it was as sweet as they get. 

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Karen

Wednesday 23rd of August 2023

In your tips,,,it said to make sure you grease your pan. The #2 step with the brown sugar and butter say mix together in bottom of pan? Whyyyy do we need to geease the pan if we are mixing the brown sugar mixture in bottom??

Julie Pollitt

Thursday 24th of August 2023

Great question! I don't like anything sticking to my pans, because it makes clean up easier. You might be able to get away with not greasing the pan, but the brown sugar will stick to the pan easily. If you don't do it on the bottom, I would definitely do it on the sides.

Harmonie

Thursday 20th of July 2023

I would like to double this cake for a thick 9×13. I have made it in a 8×8 pan and it turned out perfectly.

How long would it take to bake at 350° if I were to double the recipe?

Julie Pollitt

Friday 21st of July 2023

I haven't doubled the recipe, so I am not sure. But, I would check it at the 45 minute mark and use a cake tester or toothpick and if it comes out with batter still on it, you might need to cook 10 more minutes. Keep checking after 5 to 10 minute increments. Hope that helps! Let us know what the final time is.

Roe

Sunday 23rd of April 2023

Can you use lactose free milk??

Julie Pollitt

Monday 24th of April 2023

Hi Roe,

I am not sure. I haven't used it before with this recipe.

Kathy

Wednesday 19th of April 2023

I made this and followed the recipe exactly and it came out perfectly. It was the most delicious cake I have ever baked! My husband loved it too.

Julie Pollitt

Thursday 20th of April 2023

That's awesome! I am so glad to hear that. Thank you for sharing!

Mike

Tuesday 11th of April 2023

I had heart bypass surgery about 2 months ago, so have to lower my salt and saturated fat. I used unsalted butter in the topping. I made several substitutions in the batter. I used brown sugar for more richness. I used sodium free baking powder. Left the salt out. Replaced the milk with pineapple juice. Used slightly less avocado oil in place of the butter. I also had no cherries or Pineapple slices so I used the well drained crushed pineapple and walnut pieces and slivered almonds instead.

Julie Pollitt

Tuesday 11th of April 2023

Sounds like a great alternative! And delicious! Thank you for sharing that and hope you're on the mend. :)

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