This Duncan Hines Pineapple Upside Down Cake is soft, fluffy, and moist. Made with Duncan Hines cake mix with a beautiful topping of caramelized pineapples and maraschino cherries, this classic recipe is so easy to prepare with a secret shortcut. It might be old-fashioned, but it’s far from boring!

When I need a quick and easy dessert, I often make Bisquick Coffee Cake, Cinnamon Roll Apple Pie Cups, and this gorgeous cake mix pineapple upside-down cake.

This pineapple upside-down cake comes together in no time, using a box of Duncan Hines Cake mix. This handy shortcut ensures your cake comes out perfectly every time, without you having to start from scratch.

Ingredients and Substitutes

• Melted Butter: You’ll need melted butter to make your caramelized fruit topping. It’s better to use unsalted butter.
• Brown Sugar: Brown sugar gives the best flavor to this cake, but you may substitute it with white granulated sugar.
• Pineapple Slices: Use canned pineapple slices, available in any grocery store. If you have fresh pineapples, feel free to use them.
• Maraschino Cherries: These bright red cherries are syrupy sweet and can be found in the baking aisle.
• Duncan Hines Cake Mix: This classic cake mix can be found in any supermarket. Look for the bright red box.
• Other ingredients called for on the box including water, oil, and eggs.

How to Make Duncan Pineapple Upside Down Cake

Step 1: Prepare the Topping

• Pour melted butter into a 9-inch pie plate. Spread the butter evenly to cover the entire bottom.
• Sprinkle brown sugar evenly on top of the butter.
• Add pineapple slices on top of the brown sugar.
• Place maraschino cherries in the center of pineapple slices. Set aside.

Step 2: Prepare the Cake Batter

• Prepare the cake batter according to the instructions on the package
• Pour and spread the cake batter evenly over the topping.

Step 3: Bake & Flip the Cake

• Bake for 45-50 minutes. Loosely cover with foil after 30 minutes to prevent the top from over-browning.
• Remove the cake from the oven and let it cool for about 15 minutes. Then carefully invert the cake onto a serving plate.

Tips & Tricks

• Room temperature ingredients: Any pastry chef will tell you that using room temperature ingredients results in a soft and fluffy cake. Take your eggs and other ingredients out of the fridge and let them get to room temperature before you start mixing.
• Make sure your cake pan is deep enough: To prevent the cake batter from overflowing, you’ll need a cake pan that’s at least 2-inch deep.
• Dry pineapple slices: Drain the juice from the canned pineapples, then use a paper towel to get rid of excess liquid from the slices. Doing this prevents the cake batter from overflowing during baking.  You also don’t want a wet, soggy cake.
• Don’t grease the pan: because of how buttery the cherry-pineapple topping is, there’s no need to grease the pan.

Duncan Hines Pineapple Upside Down Cake Topping

The caramelized cherry pineapple topping is the star of the show! You’ll need melted butter, brown sugar, pineapple slices, and maraschino cherries. Be sure to drain the pineapple juice and use a paper towel to dry the slices before putting them into your baking pan. We also recommend refrigerating the topping before pouring in the batter for the best result.

How to Flip the Baked Pineapple Upside-down Cake

After all your hard work, it’s time for the big reveal! Flipping your pineapple upside-down cake is a simple, but critical step. You must allow the cake to cool for 10-15 minutes after removing it from the oven. Use a knife to gently loosen any of the cake that may be baked onto the edge of the pan. Place a large plate on top of the pan and, using oven mitts (as it’ll be VERY hot), flip the cake over in one firm, swift motion. Set your plate down and carefully slide the pan off.

Can I Substitute Pineapple Juice for Water in the Cake Mix?

No, we don’t recommend doing this. You may be tempted to use pineapple juice to improve the flavor of your cake. Instead, this results in a cake that is overly sweet with a soggy texture. Just use water for this recipe.

How Can I Keep Pineapple Upside Down Cake from Getting Soggy?

The number one way to avoid a soggy cake is to dry your pineapple slices. If using canned pineapples, drain the juice and use a paper towel to pat dry any excess liquid. Remember not to use any pineapple juice when mixing the cake batter.

Variations

Pineapple Upside Down Cupcakes

These adorable cupcakes are miniature versions of a classic. This is made in the same way as the full-size cake, but you will instead use a muffin tin. Use one pineapple slice and one cherry as the topping for each cupcake.

Pineapple Upside Down Bundt Cake

If you prefer, this cake can be made in a Bundt pan. The procedure is the same, but the shape of the cake is an interesting variation on this fruity dessert.

Pineapple Upside Down Cake with Vanilla Pudding

Looking for a richer, moister version of this cake? Adding vanilla pudding to the mix creates a creamier, thicker batter and a cake with a pudding-like texture.

If You Like This Recipe Try These Out

If you tried this recipe, let me know how your Pineapple Upside Down Cake turns out in the comments below!