This Pineapple Upside Down Cake with Cake Mix is an easy recipe with all the classic, retro flavor and almost none of the work. The buttery brown sugar topping, perfectly placed pineapple rings, and bright maraschino cherries all bake into a 9×13 pan you can flip out onto a platter and serve to a crowd.

Pineapple upside down cake with cake mix on a white platter, topped with pineapple rings and maraschino cherries.

Making pineapple desserts like my Pineapple Angel Food Cake and this one is a longstanding tradition around here once the warmer weather rolls in.

I don’t particularly want to spend hours baking, but I absolutely want to eat cake. So quick, simple recipes like this one (or my Lemon Bundt Cake with Cake Mix and Orange Juice Cake) are my go-tos.

A square slice of pineapple upside down cake on a white plate with a pineapple ring and a maraschino cherry on top.

It’s perfect for summer cookouts, family birthdays, and potlucks where you need a dessert that feeds 12 without much fuss.

Why you’ll love this recipe

10 minutes of prep. The boxed cake mix does the heavy lifting.
Tastes like the classic. Brown sugar, butter, pineapple, and cherries hit all the notes you remember.
Family favorite. A reliable crowd-pleaser at potlucks, pool parties, and Sunday dinners.
Cold or warm. Eat it straight from the fridge or microwave a slice for 15 to 20 seconds.

Ingredients

This section includes ingredient notes and substitution options. Get all measurements, ingredients, and instructions in the printable recipe card at the end of this post.

Unsalted butter and light brown sugar — Melt the butter and stir it with the packed brown sugar to make the caramel topping that sits at the bottom of the pan. Pack the brown sugar firmly when measuring.
Pineapple slices in juice and maraschino cherries — A 20-ounce can of pineapple and a 6-ounce jar of stemless cherries. Drain both, pat them dry, and reserve the pineapple juice for the cake batter. Drying the cherries keeps the color from bleeding into the cake.
Yellow cake mix, vegetable oil, and eggs — A 15.25 oz box of yellow cake mix prepared per the package instructions, with the reserved pineapple juice swapped in for the water. I use Duncan Hines.

How to Make Upside Down Pineapple Cake with Cake Mix

This section shows you how to make the recipe with step-by-step photos and instructions. For the full printable recipe, see the recipe card below.

Step 1: Mix the melted butter and brown sugar, then spread it evenly into the bottom of a greased 9×13 baking pan. This becomes the caramel topping once the cake is flipped.

Step 2: Drain the canned pineapple over a measuring cup and reserve the juice. Pat the pineapple slices dry. Arrange the pineapple rings in the brown sugar mixture, adding a cherry (also pat dry) into the center of each pineapple slice.

A hand placing a maraschino cherry into the center of a pineapple ring among other arranged rings in a pan.

Step 3: Add water to the reserved pineapple juice to make 1 cup total and use it to prepare the cake mix, along with the oil and eggs. Pour the batter evenly over the pineapple and cherries.

Yellow cake batter being poured over pineapple slices and cherries in a 9x13 baking pan.

Step 4: Bake for 35 to 40 minutes, until a toothpick inserted in the center comes out clean.

Step 5: Once out of the oven, run a butter knife around the edges to loosen, and flip it over onto a plate while it is still warm. Place a heatproof platter on top, flip, then wait 5 minutes before lifting the pan off. Let the cake cool for 30 minutes before slicing.

Pro Tip:

The flip happens while the cake is still hot, but the resting step is what saves you. Place a heatproof platter on top, flip the whole thing over, and let it sit for 5 minutes before lifting the pan straight up. The caramel topping releases cleanly when you give it that pause.

A slice of pineapple upside down cake being lifted on a metal serving spatula from the pan.

Storage

Refrigerator: Cover tightly with plastic wrap or transfer slices to an airtight container. The cake keeps in the fridge for up to 3 days.

Freezer: Wrap the whole cake (or individual slices) tightly in plastic wrap and a layer of foil. Freeze for up to 3 months and thaw overnight in the fridge before serving.

How to Reheat: This easy pineapple upside-down cake recipe can be enjoyed cold, but if you prefer that soft, buttery texture, pop it in the microwave for a few seconds.

Tips for the Best Pineapple Upside Down Cake

Pat the pineapple slices and cherries dry before placing them in the pan. Excess moisture thins the topping and can cause the cherry color to bleed.
Spread the brown sugar mixture into an even layer so the topping on the top of the cake comes out smooth and glossy.
Use a light-colored metal cake pan. Dark metal pans tend to brown the bottom too quickly.
Don’t overmix the cake batter. A few lumps are fine and keep the cake tender.
If you don’t have a large platter, a flat baking sheet or sturdy cutting board works fine. Make sure whatever you flip onto is heatproof and has a lip or rim to catch the syrup.

Overhead view of finished pineapple upside down cake with rows of cherry-centered pineapple rings in a brown sugar glaze.

More Cake Mix Desserts

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Square plated slice of pineapple upside down cake with a pineapple ring and a cherry on a white dish.

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