Pineapple Upside Down Cake

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Pineapple upside-down cake is a nostalgic and easy-to-make dessert that’s equally at home on your dinner table, around a campfire, or at a picnic. 

picture of pineapple upside down cake with a pineapples and maraschino cherries baked onto the top
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picture of a slice of pineapple upside down cake with a pineapples and maraschino cherries baked onto the top

Easy Pineapple Upside Down Cake

Pineapple upside-down cake is such an easy, classic American dish that will please your whole family.

Recipes for pineapple upside-down cake first started appearing in America in the 1920s and exploded in popularity when the Dole fruit company asked for pineapple recipes to be submitted by Americans. Over 2,500 variations on the pineapple upside-down cake were allegedly submitted to Dole by Americans. 

The style of upside-down cake is a spin-off of the classic French Tarte Tatin and the Brazilian or Portuguese bolo de ananás – which both involved the toppings being added to the bottom of a pan, before being flipped “upside down” before serving. 

My husband’s grandfather would always make this in a dutch oven when they were camping or at scout camp, so this dish holds a strong sentimental place in our family. It’s delicious, so we keep making it!

picture of pineapple upside down cake with a pineapples and maraschino cherries baked onto the top

How to Make Pineapple Upside Down Cake

To make this recipe, you’ll need:

  • Butter – Every dish needs some fat to provide flavor. Butter when cooked provides a mild, nutty flavor and a rich, decadent mouthfeel to desserts like this.
  • Brown Sugar – Brown sugar gets its name and appearance from the small amount of molasses that remains in the refined sugar. Light brown sugar contains only 3.5% molasses while dark brown sugar contains 6%. I used light brown sugar for this recipe.
  • Canned Pineapple Slices – The fruit and juice from canned pineapple rings give the dish its name. Pineapple is served across the globe, but its popularity has skyrocketed with the European Union consuming 50% of the world’s pineapple in the mid 2010s.
  • Maraschino Cherries – These electric red fruits are preserved, sweetened cherries. They’re first brined to bleach them and then soaked in food coloring, sugar syrup, and sometimes alcohol. I used generic, non-alcoholic maraschino cherries for this dish.
  • Yellow Cake Mix – I used the Betty Crocker Super Moist Yellow Cake Mix. Boxed cake mix is an easy way to make this classic recipe in a flash.
  • Eggs and butter– You’ll need eggs and oil or butter depending on the ingredients needed to complete the boxed cake mix. Instead of the water needed for the boxed mix, you’ll use the canned pineapple juice for a kick of pineapple flavor.

Once you’ve gathered your ingredients, we will use the following method: 

  • Prepare your baking dish. In a greased, 9X13 baking dish spread your brown sugar evenly across the bottom of the dish. Arrange your pineapple rings on top of the brown sugar around your pan. I did it in rows, but you could be fancy and try a design. Then place your drained maraschino cherries in the middle of each pineapple ring and between the rows of pineapple in a decorative manner. Gently press the pineapple and cherries into the brown sugar once they are arranged in the baking dish.
  • Mix cake.  Follow the directions on your box of cake mix, substituting the water called for with the liquid from your can of pineapple rings. If you’re short the required amount of liquid, add water. Gently add the cake mix to your baking sheet with the pineapple, cherries, and brown sugar, being careful not to mess up the arrangement of the pineapple rings. Gently tap the baking dish on your countertop a few times to settle the baking mix evenly and ensure no air bubbles. 
  • Bake. In a 350oF oven, bake your pineapple upside-down cake for 40-45 minutes until it is golden brown and an inserted toothpick comes out clean. Once removed from the oven, run a sharp knife around the sides and corners of the pan to loosen it from the baking dish. 
  • Flip and enjoy.  When the baking dish has cooled down slightly, place your serving platter or a parchment paper-lined baking sheet upside down on top of the baking dish. In one fluid motion, flip over the baking dish onto your platter or sheet pan to “flip” the cake upside down and out of the baking dish. Enjoy warm with a hot cup of coffee or adorned with whipped cream or vanilla ice icecream. 
picture of pineapple upside down cake with a pineapples and maraschino cherries baked onto the top

Tips and Tricks to Perfect Pineapple Upside Down Cake & FAQs

Classic Pineapple Upside down Cake is an incredibly easy recipe to make, but these tips will help you make it even easier.

Don’t throw away the canned pineapple liquid. The liquid from the canned pineapple rings will be used to replace the water needed for the boxed cake mix. It will add even more moisture and pineapple flavor to the cake.

Go fancy on the cherries to add some flair to your cake. If you want to kick up the flavor, and bring a bit more flair to your cake presentation, use Luxardo maraschino cherries, or artisanal, alcohol-soaked cocktail cherries. Bourbon cherries from Jack Rudy are a great choice. 

Fully commit to the flip.  Flipping the cake “upside down” out of the baking dish is easier than it sounds, you just have to fully commit to it. If you stop half-way or slow down during the flip, you’re gonna make a mess. Flip it smoothly and decisively and you’ll be in good shape.

FAQ:

Can I substitute crushed pineapple?

Yes! If you can’t find pineapple rings, you can use crushed pineapple, which you’ve drained and reserved the liquid from. You’ll want to be more artistic with the arrangement of your cherries if you use crushed pineapple. 

Should pineapple upside down cake be refrigerated?

If not consumed within 48 hours, you should refrigerate your pineapple upside-down cake. If your kitchen is hotter than 70oF you should refrigerate it immediately.

Is this recipe gluten free?

The recipe is not gluten-free if you use the Betty Crocker cake mix I suggested. However, you can substitute a gluten-free yellow cake mix like this one to make it gluten-free. 

picture of pineapple upside down cake with a pineapples and maraschino cherries baked onto the top

What to Serve With Easy Pineapple Upside Down Cake

This easy pineapple upside-down cake is a great dessert for ANY dinner. I like to serve it with a decaf espresso and a dollop of whipped cream!

This is such a classic mid-century American dish, I love it with my easy smashed burgers or bacon-wrapped hotdogs.

It’s also a great winner desert paired up with classic chili

For more of our favorite cookout dinners and BBQ recipes that are good all year long, find our favorites below:

picture of pineapple upside down cake with a pineapples and maraschino cherries baked onto the top

Pineapple Upside Down Cake Recipe

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picture of pineapple upside down cake with a pineapple and maraschino cherry baked onto the top

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picture of pineapple upside down cake with a pineapple and maraschino cherry baked onto the top
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Pineapple Upside Down Cake

Delicious classic pineapple upside down cake is a classic the whole family will love!
Course Desserts
Cuisine American
Keyword baking, cake, cake mix varieties, cherries, dessert, easy cake, pineapple, yellow cake mix
Prep Time 10 minutes
Cook Time 45 minutes
Additional Time 5 minutes
Total Time 5 minutes
Servings 12 servings
Calories 440kcal
Author Courtney O’Dell

Ingredients

  • 1 box Yellow Cake Mix
  • 1 can of pineapple slices drained (reserve the juice)
  • ¼ cup butter
  • 1 cup packed brown sugar
  • 1 jar small jar of maraschino cherries without stems drained
  • Butter and eggs as called for on cake mix box

Instructions

  • Preheat eat oven to 350°F. 
  • Melt the butter. 
  • In a 9X13 glass baking dish, pour the melted butter, then add thebrown sugar evenly across the dish.
  • Arrange pineapple slices in rows on top of the brown sugar. Place a maraschino cherry in center of each pineapple slice, and place the rest of the cherries decoratively around the slices and the outside of the pan.
  • Gently press the pineapple and cherries into brown sugar.
  • In a bowl, follow the directions on the boxed cake mix to make your batter. Substitute the pineapple juice mixture for the water required in the recipe. If the pineapple juice is less than the amount of liquid needed for the box recipe, add water. 
  • Softly pour the batter over pineapple and cherries trying to void distribution the arrangement of the fruit.
  • Bake for 40-45 minutes or until toothpick inserted in center comes out clean. 
  • Run a butter knife around side of pan to loosen cake.  When the baking dish has cooled down slightly, place your serving platter or a parchment paper-lined baking sheet upside down on top of the baking dish. In one fluid motion, flip over the baking dish onto your platter or sheet pan to “flip” the cake upside down and out of the baking dish.
  • Leave the baking dish on top of the upside down cake to allow the brown sugar glaze to drip on to the cake.  Allow to cool.  Serve warm or cool according to your preference.  Store in your refrigerator.

Nutrition

Serving: 1g | Calories: 440kcal | Carbohydrates: 88g | Protein: 4g | Fat: 8g | Saturated Fat: 5g | Polyunsaturated Fat: 2g | Cholesterol: 28mg | Sodium: 684mg | Fiber: 1g | Sugar: 54g

About Courtney

Courtney loves to share great wine, good food, and loves to explore far flung places- all while masting an everyday elegant and easy style at lifestyle blog Sweet C’s Designs. Sweet C's devoted to finding the best food and drinks you'll want to make or find, around the world!

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2 Comments

  1. Marge says:

    Can I use Canned peaches, instead of pineapple?

    1. Courtney ODell says:

      The flavor will be completely different, but you definitely can!