My Easy Pineapple Upside Down Cake is the Retro Dessert You Need To Make

A classic made super easy.

By
Molly Allen
Molly Allen
Molly Allen
Molly Allen is a writer and editor with a focus on food, beverage, travel, adventure, and lifestyle content, A former bakery owner, her work spans kitchen guides, food and beverage round-ups, recipe development, etc. She's featured in Taste of Home, Good Housekeeping, Insider, Brides, Simply Recipes, and more.
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Published May 01, 2025
Molly Allen
Easy Pineapple Upside Down Cake on a plate, one slice removed, another slice cut

Simply Recipes / Molly Allen

If there’s one cake that will never go out of style for me, it’s pineapple upside down cake. Dating back to the 1920s, this colorful cake has been a dessert staple for decades. It’s exactly what comes to mind when I think of retro cakes, and one that has stood the test of time for good reason.

While there’s a time and place for a frosted layer cake, I love a cake that doesn’t actually need frosting as a finishing touch. By making a brown sugar mixture with slices of flavorful pineapple and pouring the batter over the top, you create an ideal gooey topping to adorn the cake—no frosting (or extra dirty dishes) required. It’s visually stunning and the blend of flavors melds together perfectly in every bite.  

This recipe uses boxed cake mix as a shortcut to produce the easiest-ever pineapple upside down cake. You can prep it in 15 minutes flat while the oven preheats—a total win!

Easy Pineapple Upside Down Cake on a cake plate

Simply Recipes / Molly Allen

The Trick for Flipping Pineapple Upside Down Cake

The appeal of an upside down cake is all in the topping—the last thing you want to do is ruin it when it comes time to remove the cake from the pan. The secret to success is all in the timing. 

Once you have removed the cake from the oven, set a timer for 10 minutes. At the 10-minute mark, use a butter knife or offset spatula to loosen the sides of the cake from the pan, then invert it onto a cake plate or serving platter. Give the pan a little jiggle for a clean release. 

Letting the cake cool in the pan for longer than 10 minutes runs the risk of the topping sticking to the cake pan.

Ways To Customize Pineapple Upside Down Cake

  • Try another fruit: Pineapple brings vibrant flavor and color to an upside down cake, with maraschino cherries adding a pop of contrasting red. While it’s a classic combination, it’s not the only option. This recipe can be adapted to use sliced peaches or pears, berries, and fresh pitted cherries. If you do skip the pineapple slices, omit the pineapple juice in the batter and use all water instead.
  • Add nuts: Play with the texture of your cake. Sprinkle 1/2 cup of chopped pecans or walnuts over the topping before pouring over the batter. You could also choose to fold the nuts into the batter to incorporate crunch throughout.
Easy Pineapple Upside Down Cake, one slice removed and plated

Simply Recipes / Molly Allen

More Retro Cakes

Easy Pineapple Upside Down Cake

Prep Time 15 mins
Cook Time 50 mins
Cool: 10 mins
Total Time 75 mins
Servings 8 to 10 servings
Yield 1 (9-inch round) cake
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Ingredients

  • Nonstick cooking spray

  • 1/2 cup (100g) packed dark brown sugar

  • 5 tablespoons unsalted butter, melted

  • 1 (20-ounce) can pineapple slices in juice, drained, with 1/2 cup juice reserved

  • 7 maraschino cherries

  • 1 (15.25-ounce) package yellow cake mix

  • 2 large eggs

  • 1/2 cup vegetable or canola oil

  • 1/2 cup water

Method

  1. Preheat the oven to 350°F.

    Lightly grease a 9-inch round cake pan that’s at least 2 inches tall with nonstick cooking spray.

  2. Make the topping:

    In a small bowl, whisk the brown sugar and melted butter until smooth. Spread the mixture evenly into the bottom of the cake pan.

    Arrange a single layer of pineapple slices on top of the brown sugar mixture in the cake pan, cutting smaller pieces to fill in gaps as needed. Place a maraschino cherry in the center of each pineapple slice.

  3. Make the cake batter:

    In a large bowl, beat together the cake mix, eggs, oil, water, and reserved pineapple juice until smooth. Pour the batter over the pineapple slices and cherries.

  4. Bake:

    Bake the cake until the top is golden brown and a toothpick or cake tester inserted in the center comes out clean, 45 to 55 minutes.

  5. Turn out the cake:

    Cool the cake in the pan for 10 minutes. Gently run a butter knife or offset spatula around the sides of the pan and turn the cake out onto a plate or platter while it’s still warm. Let cool completely before serving.

    Store the cake covered or in an airtight container at room temperature for up to 2 days or in the refrigerator for up to 4 days.

    Love the recipe? Leave us stars and a comment below!

Nutrition Facts (per serving)
400 Calories
19g Fat
55g Carbs
3g Protein
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Nutrition Facts
Servings: 8 to 10
Amount per serving
Calories 400
% Daily Value*
Total Fat 19g 25%
Saturated Fat 5g 27%
Cholesterol 52mg 17%
Sodium 334mg 15%
Total Carbohydrate 55g 20%
Dietary Fiber 1g 4%
Total Sugars 38g
Protein 3g
Vitamin C 6mg 29%
Calcium 116mg 9%
Iron 1mg 7%
Potassium 131mg 3%
*The % Daily Value (DV) tells you how much a nutrient in a food serving contributes to a daily diet. 2,000 calories a day is used for general nutrition advice.
Nutrition information is calculated using an ingredient database and should be considered an estimate. In cases where multiple ingredient alternatives are given, the first listed is calculated for nutrition. Garnishes and optional ingredients are not included.