BEST Pineapple Upside Down Cake

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5 from 3 votes

Let’s bring back this retro vanilla cake that’s super moist and topped with pineapple slices tucked into a generous caramelized brown butter and sugar topping. It’s called pineapple upside down cake and it’s out-of-this-world delicious!

The Best Pineapple Upside Down Cake Recipe

My husband always rolled his eyes when I’d say I’m making a fruit dessert like Strawberry Pound Cake or a Peach Crisp. He insisted that if he’s going to have dessert, why put fruit in there! But what sweet treat turned Mr. No Fruit into a fan? This pineapple upside down cake! Sure, this cake has the butter of a whole cow in it and a fair amount of sugar, but let’s call it a win. He LOVED it.

The secret to the best pineapple upside down cake is a thin, tender, moist cake that’s not so thick that it distracts from the best part: the caramelized pineapple layer. Because let’s be honest, we’re all here for that buttery brown sugar topping, aren’t we?

P.S. It’s almost a crime to not serve this cake right out of the oven. Because once you flip this bad boy, it looks and smells and tastes so good, you’ll wish you made two.

What is Pineapple Upside Down Cake?

Pineapple upside-down cake is a classic! It starts with a buttery yellow cake baked on top of a beautiful layer of caramelized pineapple slices and maraschino cherries. After baking, the cake is inverted onto a serving plate, revealing that layer of fruit that’s been bathing in caramelized brown sugar and butter like a French Tarte Tatin.

What varies between recipes is often the cake itself. The highlight of this recipe is the cake-to-topping ratio. If I do say so myself, it’s perfection. The cake layer is thin like a tart, so it absorbs all of that buttery, caramelized goodness from the pineapple topping. Moist and tender like my Olive Oil Cake with a hint of vanilla, the cake itself isn’t an afterthought in this recipe!

And the Pineapple Upside Down Cake Topping

But let’s talk about the true star of the show for a second. The topping truly does deserve its own section. Made simply by browning butter and adding brown sugar, vanilla and salt to it, the smell of this topping alone is enough to win over the biggest upside down cake skeptic. Layer on those pineapple rings (and cherries if you want) and they’ll become one with that brown butter and sugar layer.

Ingredients You Need

Here are the ingredients needed to make the moistest, most tender, buttery, AND caramelized pineapple upside down cake you’ll ever taste:

  • Can of pineapple slices in juice – while I usually wouldn’t push for using canned over fresh, canned pineapple is a must for this recipe. Canned pineapple has been marinating in its juices which makes for a perfect, tender pineapple layer. Plus you’ll want to use some of that juice to make the cake itself too. Look for pineapple slices (rings) in 100% pineapple juice.
  • Maraschino cherries (optional) – cherries are a classic component in pineapple upside down cake. Don’t like them? Don’t use them.
  • All-purpose flour – regular flour is the base of a great cake.
  • Unsalted butter – want that rich layer of caramelized pineapple on top of the cake layer? You need butter and more butter to do that!
  • Light brown sugar – light brown sugar will create the caramelization.
  • Granulated sugar – regular sugar sweetens the cake itself. We don’t want to use too much since we’re adding sweet pineapple juice too.
  • Large Egg – an egg helps the whole thing stay together.
  • Vanilla extract – you can’t beat the taste of real vanilla extract.
  • Baking powder – a little dash will help the cake rise just enough.
  • Salt – salt for flavor, people.
Pineapple upside down cake ingredients

How to Make This Pineapple Upside Down Cake

Let’s make the perfect pineapple upside down cake! Full instructions in the recipe card; this is an outline.

  1. Prep.

    Preheat oven to 350 degrees. Grease a 9” cake pan.

  2. Brown.

    In a pot, add butter for the topping. Over medium-high heat, brown butter by letting it melt, bubble, and then swirl it around until it turns nut brown.Brown butter

  3. Mix.

    Remove from heat. Add in brown sugar, salt, and vanilla. Stir.

  4. Spread.

    Spread mixture evenly in the bottom of the cake pan.Add brown butter and sugar topping to cake pan

  5. Design.

    Pat dry the pineapple and cherries. Add pineapple slices decoratively to the top of the sugar/butter layer. Then place cherries in the centers of the pineapple rings.Add pineapple rings and cherries.

  6. Cream.

    In the bowl of a mixer, add softened butter and granulated sugar. Cream them together on medium speed until fluffy.Cream together butter and sugar for cake.

  7. Add.

    Scrape down sides of the bowl. Add in the egg and vanilla. Stir.

  8. Blend.

    In a separate bowl, whisk together flour, baking soda, and salt for the cake.Whisk together dry ingredients.

  9. Combine.

    Add dry ingredients to wet ingredients and mix until just combined, scraping down the sides of the bowl.

  10. Stir.

    Add pineapple juice. Mix until just combined.Add pineapple juice to cake batter.

  11. Spread.

    Disperse batter throughout the cake pan. Use the back of a spatula and your fingers to very gently spread the batter into a thin, even layer so the fruit and butter/sugar layer are completely covered.Spread batter.

  12. Bake.

    Bake cake for 25-29 minutes, until the top is set.Bake cake.

  13. Cool.

    Let cool for 15 minutes.

  14. Invert.

    Gently run a knife around the edges of the cake pan. Flip the cake onto the plate/stand. Enjoy right away, warm, for best results.

Tip: How to Flip Pineapple Upside Down Cake

Let’s flip this thing! Here’s how to easily invert your pineapple upside-down cake:

  1. Cool slightly: Let the cake cool in the pan for 15 minutes.
  2. Loosen edges: Run a knife around the edges of the cake to loosen it.
  3. Prepare plate/stand: Place a serving plate over the cake pan.
  4. Flip: Hold the plate and pan together, then quickly flip them over.
  5. Remove pan: Lift the pan off slowly. If the cake sticks, tap the bottom.
  6. Adjust toppings (if needed): If any toppings stick to the pan, place them back on the cake!
How to invert cake

Watch How to Make It

Frequently Asked Questions

How do I prevent the cake from sticking to the pan?

Grease it! Well grease the bottom and sides of the pan so nothing sticks. If a cherry or two sticks, you can gently place them back onto the cake…no sweat!

How do I store pineapple upside down cake?

After it cools completely, store in the fridge for up to 5 days. You can only keep pineapple upside down cake at room temp for 1 day.

Can I make pineapple upside down cake in advance?

Yes, you can, but it’s best enjoyed right out of the oven if at all possible! To reheat, place the cake or slices in a 300-degree oven for 5-10 minutes. You can also microwave a slice for 20-30 seconds in a pinch.

Can I freeze it?

I don’t recommend freezing pineapple upside down cake.

Should I use canned or fresh pineapple?

Canned is the way to go. The rings are extra tender; plus, we’ll be using the pineapple juice in the can for the cake batter!

Can I use a different type of pan?

I don’t recommend using a different pan. A 9-inch cake pan is the way to go!

Best Pineapple Upside Down Cake

Let’s bring back this retro vanilla cake that’s super moist and topped with pineapple slices tucked into a generous caramelized brown butter and sugar topping. It’s called pineapple upside down cake and it’s out-of-this-world delicious!
5 from 3 votes
Prep Time: 30 minutes
Cook Time: 30 minutes
Cool Time: 15 minutes
Total Time: 1 hour 15 minutes
Course: Dessert
Cuisine: American
Keyword: fall, spring, winter
Servings: 8 slices
Calories: 315kcal
Author: Tastefully Grace

Equipment

  • 9" round cake pan
  • Stand mixer (or hand mixer)

Ingredients

The Topping

  • 20 ounce can pineapple slices in juice 7-8 rings
  • 7-8 maraschino cherries optional
  • 4 tablespoons (1/2 stick) unsalted butter
  • ½ cup light brown sugar packed
  • 1 teaspoon vanilla extract
  • teaspoon salt

The Cake

  • 1 cup all-purpose flour
  • 8 tablespoons (1 stick) unsalted butter, softened
  • cup granulated sugar
  • ¼ cup pineapple juice from can
  • 1 large egg
  • 1 teaspoon vanilla extract
  • ½ teaspoon baking powder
  • ¼ teaspoon salt

Instructions

  • Preheat oven to 350℉. Well grease a 9” round cake pan.
  • For the topping: In a small pot, add 4 tablespoons butter. Over medium-high heat, brown butter by letting it melt, bubble, and then swirl it around until it turns nut brown.
  • Once browned, remove from heat. Add in brown sugar, 1/8 teaspoon salt, and vanilla (it may spatter…be careful!). Stir until combined.
  • Spread mixture in the bottom of the cake pan as evenly as possible. It’s ok if the butter separates a bit from the sugar.
  • Pat dry the pineapple slices and cherries. Add pineapple slices decoratively to the top of the brown sugar/butter layer. Then place cherries in the centers of the pineapple rings. Set aside.
  • For the cake: In the bowl of a mixer, add softened butter and granulated sugar. Cream them together on medium speed until fluffy, about 1 minute.
  • Scrape down sides of the bowl. Add in the egg and vanilla. Stir until combined.
  • In a separate bowl, whisk together flour, baking soda, and ¼ teaspoon salt.
  • Add dry ingredients to wet ingredients, and mix until just combined, scraping down the sides of the bowl as needed.
  • Add pineapple juice. Mix until just combined.
  • Disperse batter throughout the cake pan. Use the back of a spatula and your fingers to very gently spread the batter into a thin, even layer so the fruit and butter/sugar layer are completely covered. This may take some time and patience, but it will be worth it!
  • Bake cake for 25-29 minutes, until the top of the cake is set and light golden.
  • Let cool for 15 minutes.
  • Gently run a knife around the edges of the cake pan to loosen the cake. Place a plate or cake stand on top of the cake and quickly flip (invert) the cake onto the plate/stand. Enjoy right away, warm, for the best pineapple upside down cake ever.

Video

Notes

  • Look for a can of pineapple slices (rings) in 100% pineapple juice.
  • Grease your pan well (the sides, corners, and bottom).
  • The time it takes for butter to brown depends on the brand of butter (typically 5-9 minutes).
  • What to expect: this cake will be thin, buttery and delicate with a lovely caramelized layer of pineapple and cherries. It is the perfect ratio of cake to pineapple topping and is SO good!
  • While it’s best to enjoy the cake right away, you can reheat in a 300-degree oven for 5-10 minutes until warm.

Nutrition

Serving: 1slice | Calories: 315kcal | Carbohydrates: 37g | Protein: 3g | Fat: 18g | Saturated Fat: 11g | Polyunsaturated Fat: 1g | Monounsaturated Fat: 5g | Cholesterol: 68mg | Sodium: 151mg | Potassium: 62mg | Fiber: 1g | Sugar: 24g | Vitamin A: 561IU | Vitamin C: 1mg | Calcium: 41mg | Iron: 1mg
Tried this recipe?Let us know how it was!
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6 Comments

  1. Anonymous
    May 26, 2024 / 3:30 pm

    5 stars
    This cake was incredibly moist and delicious. It reminds me of my grandmother’s! Thank you for an fantastic and easy cake I can make that my entire family loves!

    • May 28, 2024 / 8:46 am

      Aw what a compliment! Thank you so much for your review 🙂

      Grace

  2. Anonymous
    May 24, 2024 / 8:58 am

    5 stars
    The amazing feature of this retro cake is the cake itself. It’s the moistest, butteriest yellow cake I’ve ever tasted. Together with the pineapple brown sugar topping, it’s upside down cake taken to another level!

    • May 24, 2024 / 10:37 am

      Woohoo! I love your description of the cake. I totally agree!

      Grace

  3. Anonymous
    May 23, 2024 / 3:27 pm

    5 stars
    This is seriously one of the best cakes ever! The ratio of cake to pineapple topping is perfection.

5 from 3 votes

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