Pineapple Upside Down Cake

This Pineapple Upside Down Cake is soft and buttery with caramelized pineapple and cherries, and it is just what you need to impress your guests! And, contrary to popular belief, it’s a not a difficult cake to make!

Aerial view of pineapple upside down cake

The Best Pineapple Cake

This cake has been a long time coming. I’m a big fan of pineapple upside down cake and so is my dad and I’ve been wanting to make my own delicious version. The pressure was on to make one that was just right. Naturally I started with my trusted moist vanilla layer cake. That cake is such a gem and adapts beautifully to so many things.

I did make some adjustments to that cake, starting with the recipe and pan size. This cake is half of the recipe and fits in a 9-inch pan. Plus, to have the right amount of batter, the right flavor and the ideal result, I made a few other changes, such as reducing the flour and baking powder a bit and adding brown sugar and a little pineapple juice. I tried the cake without the pineapple juice and found the flavor to be exponentially better with just a bit of extra pineapple flavor from the juice. The brown sugar was the same – the cake just lacked a little flavor with only granulated sugar.

This cake is moist and dense, like pineapple upside down cake should be. But it’s not heavy and it’s wonderfully tender. The flavor is perfection! I’m so in love with it and know that I’ll make this classic version over and over. SO good!

A pineapple upside down cake with cherries

What You’ll Need

As I mentioned, this pineapple cake uses many of the same ingredients as a homemade vanilla cake, with a few changes. Plus, of course, the addition of pineapple and pineapple juice.

For the Topping

  • Butter – The butter used in the topping should be melted.
  • Brown sugar – To help caramelize the pineapple.
  • Pineapple slices – I use canned pineapple so that I have the juice for the cake, but you can use fresh pineapple as well.
  • Maraschino cherries – The perfect compliment to pineapple and adds a pop of color. Be sure to drain and dry them first!

For the Cake

  • All-purpose flour – A pantry staple.
  • Baking powder – Helps the cake rise and create the fluffy texture.
  • Salt – For flavor.
  • Unsalted butter – Make sure it’s room temperature.
  • Vegetable oil – For extra moisture.
  • Sugar & Brown Sugar – I found a combination of both to be important, without the brown sugar the flavor was just too bland.
  • Vanilla extract – For flavor.
  • Eggs – Large eggs.
  • Milk – I use 2%, but whole milk would work too.
  • Pineapple juice – For tasty pineapple flavor in every bite!
A slice of pineapple upside down cake

How to Make Pineapple Upside Down Cake

Making a a pineapple upside down cake may seem complicated or overwhelming, but in reality it’s no harder than any other homemade cake! In fact, the decorating is done for you, so it’s really quite simple. Just take your time and be sure to follow the steps careful for a perfectly moist, spongey cake.

  • Prepare oven and cake pan. Preheat oven to 350F. Spread a mixture of melted butter and brown sugar on the bottoms of cake pan.
  • Add the cherries and pineapple. Drain the pineapple, reserving the juice. Pat pineapple dry and arrange the slices and cherries over the brown sugar.
  • Make the cake batter. Combine dry ingredients in a medium bowl and set aside. In a large bowl, beat the butter, oil, sugars and vanilla until light and fluffy. Add the eggs one at a time, taking care to scrape down the sides. Add half of the dry ingredients, combine, and slowly add the milk and pineapple juice. Add remaining dry ingredients and mix until well incorporated.
  • Bake. Add the batter to the cake pan and bake for 30 minutes. Cover with foil and bake an additional 10-15 minutes, until a toothpick inserted in the middle comes out clean.
  • Cool and serve. When you take the cake out of the oven, immediately cover it with a kitchen towel and then gently press down on it to help compress the dome of the cake. Let the cake cool for 20 minutes, then invert onto a cooling rack to cool more before serving. Pineapple upside down cake is best served warm.
A slice of pineapple cake

Tips for Success

There are a few key things to keep in mind when making this pineapple cake, mostly to ensure that it’s just the right amount of moisture and not too mushy.

  • Be sure to dry the pineapple slices. Whether fresh or canned, blot your pineapple slices before adding them to the pan. This cake has a delicate balance of moisture and overdoing it can end up giving you a mushy, messy cake.
  • Take the time creaming the butter and sugar. Beating the butter and sugar for 2-3 minutes helps the cake rise properly.
  • Press down on the cake. Right after taking the cake out of the oven, place a kitchen towel over the top of it and press down on it with gentle, but firm pressure. This will help compress the dome so that your cake doesn’t split down the middle when you invert it.
  • Allow to cool before inverting. Give the cake at least 15 minutes to cool in the pan before inverting it and removing the cake from the pan.
  • Use slices stored in juice – not syrup. If you’re using canned pineapple slices, be sure to grab one with juice and not syrup!
A slice of pineapple upside down cake with a bite missing

Serving Suggestions

Pineapple upside down cake should be served warm. Usually about 45 minutes after removing it from the oven, it’s the perfect temperature for eating.

It’s best served warm, but if you allow it to cool completely to room temperature, you can heat individual slices for 10-15 seconds in the microwave to warm them back up a bit.

How to Store Leftovers

Any leftover cake should be stored in the fridge. Cover it tightly with plastic wrap or in an airtight container, so that it doesn’t dry out.

I like to heat my leftovers in the microwave for 30 seconds or so, just enough to warm it up again. This is definitely one cake better served warm!

Can I Freeze This Cake?

Pineapple upside down cake is not ideal for freezing. It could become mushy and may collapse a bit from the weight of the thawed pineapples.

But, don’t worry – that’s just even more of a reason to have a second slice!

Print
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A pineapple upside down cake with cherries
Recipe

Pineapple Upside Down Cake

  • Author: Lindsay
  • Prep Time: 30 minutes
  • Cool Time: 20 minutes
  • Cook Time: 45 minutes
  • Total Time: 95 minutes
  • Yield: 810 slices 1x
  • Category: Dessert
  • Method: Baking
  • Cuisine: American

Description

Soft and buttery with caramelized pineapple and cherries, this Pineapple Upside Down Cake is just what you need to impress your guests. And, contrary to popular belief, it’s a not a difficult cake to make!


Scale

Ingredients

For the Topping

  • 1/4 cup butter, melted
  • 1/2 cup packed brown sugar
  • 10 canned pineapple slices
  • 13 maraschino cherries

For the Cake

  • 1 1/4 cups (163g) all-purpose flour
  • 1 tsp baking powder
  • 1/4 tsp salt
  • 6 tbsp (84g) unsalted butter, room temperature
  • 2 tbsp (30ml) vegetable oil
  • 1/2 cup (104g) sugar
  • 1/4 cup (56g) packed brown sugar
  • 1 1/2 tsp vanilla extract
  • 2 large eggs
  • 1/4 cup (60ml) milk
  • 1/4 cup (60ml) pineapple juice

Instructions

  1. Preheat oven to 350°F (176°C).
  2. Combine the melted butter and brown sugar and spread evenly in the bottom and up the sides of a 9×2 inch cake pan.
  3. Drain the pineapple, reserving 1/4 cup of juice. Set juice aside and pat the pineapple slices dry so that you don’t add excess liquid to the topping. Arrange the pineapple slices and cherries over the brown sugar, using the photos above for visual reference.
  4. To make the cake batter, combine the flour, baking powder and salt in a medium sized bowl and set aside.
  5. Add the butter, oil, sugars and vanilla extract to a large mixer bowl and beat together until light in color and fluffy, about 2-3 minutes. Do not skimp on the creaming time.
  6. Add the eggs one at a time, mixing until mostly combined after each. Scrape down the sides of the bowl as needed to be sure all ingredients are well incorporated.
  7. Add half of the dry ingredients to the batter and mix until mostly combined.
  8. Slowly add the milk and reserved pineapple juice and mix until well combined. The batter may look a little curdled, but that’s ok.
  9. Add the remaining dry ingredients and mix until well combined and smooth. Scrape down the sides of the bowl as needed to be sure all ingredients are well incorporated. Do not over mix the batter.
  10. Add the batter to the prepared cake pan and spread evenly. Bake for 30 minutes, then cover with foil and bake another 10-15 minutes to prevent the top from over-browning. The cake is done when a toothpick inserted in the middle comes out clean.
  11. Remove the cake from the oven and press the cake down gently to help flatten any dome. I placed a dish cloth on top of the cake to help press on the hot cake.
  12. Let the cake cool in the pan for 20 minutes, then invert onto a cooling rack. Allow the cake to cool a bit before serving. It’s best served warm, but if you allow it to cool completely to room temperature, you can heat individual slices for 10-15 seconds to warm them back up a bit.

Keywords: pineapple cake, pineapple desserts, how to make upside down cake

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Recipe rating

2 Comments
  1. Dena

    I made this yesterday for Father’s day (and my mom’s birthday) as it is my dad’s favorite cake. It was fabulous! Definitely eat it warm like suggested. Thank for a “keeper” recipe!

  2. Chrissy

    Could you do this as jumbo cupcakes? If so, would you need to alter the recipe or change quantity? About how many jumbo cupcakes would this amount of batter be?

Lindsay
About Lindsay

I'm a wife and mom to twin boys, a baby girl and a sweet black lab with a serious sweets addiction! Bring on the sugar!

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“Be joyful in hope, patient in affliction, faithful in prayer.” Romans 12:12