Easy Pineapple Upside Down Cake With Cake Mix

Aloha Pineapple Upside Down Cake! Fruity yellow pineapple cake and sweet candied cherries, drenched with a gooey butter and brown sugar pineapple glaze. Turn a boxed cake mix “upside-down” with this gorgeous tropical dessert.

Pineapple is a tasty, refreshing, and versatile participant in a slew of delicious recipes. Check out snack and party-ready Pineapple Mango Salsa, lunch or dinner Baja Shrimp Tacos With Pineapple Lime Slaw, or a refreshing Banana Pineapple Italian Ice treat! Relax after a long day or week with my crazy good Pineapple Jalapeno Margarita.

Why Upside Down Pineapple Cake Using A Cake Mix Is Great!

First, I love this pineapple upside-down cake recipe because using a boxed cake is time-saving and convenient; no measure, no mess, it’s just plain yummy! Added bonus: for bromelain-sensitive pineapple lovers, it’s a great way to enjoy this tasty tropical fruit without irritation from these pineapple enzymes (heat destroyed). It’s a true “Have your cake and eat it too” sitch! Win-win!

• Moist, melt-in-your-mouth pineapple-infused cake with the ease and convenience of a boxed cake mix.
• Pineapple upside-down cake is imbued with caramelized butter and brown sugar pineapple glaze! ‘Ono! (Hawaiin for delicious!) 
• Quick and easy to throw together.
• Transports easily for sharing: dinner parties, church socials, and office meetings.
• Gorgeous presentation for brunch, holiday dessert, or any occasion.

Ingredients For Upside Down Pineapple Cake (With A Boxed Cake Mix)

Simple to make, easy ingredients, and the convenience of a boxed cake mix. Luscious pineapple flavor, moist tender cake, and buttery sugar glaze taste like a plate of tropical sunshine using only a few ingredients!

For specific amounts, please refer to the printable recipe card at the bottom of the post.

• Butter – melted just enough to be soupy but not enough for the water and butter solids to separate.
• Light Brown Sugar – melts into the sugar, forming a wonderfully caramelized glaze for an upside-down cake pineapple topping.
• Canned Pineapple Slices – drain pineapple well* and reserve liquid for preparing the cake mix.
• Maraschino Cherries – or candied cherries are placed in the center of the pineapple rings.
• Yellow Cake Mix – prepare the cake mix according to the ingredients listed on the box: oil, egg(s), and use the reserved pineapple juice for water.

This post may contain affiliate links. Please read my disclosure policy here.

How To Make An Easy Pineapple Upside-Down Cake With Cake Mix

Simple steps, simple ingredients, simply delicious! Preheat your oven and select a heavy oven-proof skillet (a cast iron skillet works great) or baking pan. Set out your ingredients and get a mixing bowl, mixer, and a cutting board or platter. It’s go time!

When you are making this recipe, you’ll want to use the full recipe at the bottom of the page.

1. Add melted butter and brown sugar to an oven-proof skillet. 
2. Arrange pineapple and cherries over brown sugar.
3. Prepare yellow cake mix according to directions, using pineapple juice in place of water. Pour the pineapple cake batter over the fruit.
4. Bake until the cake is golden brown, springs back when touched, and a toothpick will come out clean with no wet batter ~ 40-45 minutes. 
5. Cool the pineapple upside-down cake on a cooling rack for 5 minutes. Losen the edges with a butter knife. Invert the pineapple cake onto a cutting board or platter. Leave the skillet over the cake for a few minutes to allow the brown sugar glaze to drizzle over the cake.
6. Slice and serve warm or cold.

Upside Down Pineapple Cake Recipe Notes/Tips

• Pat pineapple slices dry with a paper towel to avoid any sog in your upside-down cake.
• If you are out of brown sugar, add 1 tbsp molasses to 1 cup of white sugar and combine well.
• Some people prefer to add cherries to the top of a pineapple cake after it is baked. Either preference works, and you can leave them off if you don’t like cherries.
• If you are using a 13×9” cake metal cake pan start checking it around 35-40 minutes. Note: you will need 12 pineapple slices for this size pan.
• If the skillet scuffles with the pineapple upside down topping and wins, use a spatula to leverage the stuck bits off and strategically arrange them back onto the cake.
• If YOU have a scuffle with the spatula and the skillet, artfully arrange whipped cream rosettes on the top. For a critical triage, sprinkle the top with some coconut flakes too, and place a cherry or pecan half here and there to draw the eye.
• Disregard “scuffle” tips; I have faith in your baking skills! 😉

Pineapple Cake Variations & Additions

• Upside-down pineapple cake can also be made with well-drained chunks instead of pineapple rings. 
• Fresh pineapple rings are delicious and create a different flavor profile with a slight textural shift for pineapple upside-down cakes. 
• White sugar can be substituted for brown sugar glaze if necessary.
• Add ¼ teaspoon almond extract to the cake batter for added flavor.
• For a tropical nuance, use coconut oil instead of vegetable oil for a slight coconut flavor when preparing the boxed cake mix with pineapple juice. 
• Add pecan or walnut halves in patterns between the pineapple slices, or sprinkle pieces.
• Maraschino cherries can be chopped and added to the batter to create a “cherry-chip” appearance for a pineapple cake.
• When using a 10-inch skillet, the pineapple cake batter will be thicker and might need more baking time. Check pineapple upside-down cake for doneness at 5-minute increments, starting at the 40-minute mark until done.

Upside-Down Cake Serving Suggestions

Thanks to Jimmy Dole and his turn of the 20th-century entrepreneurial spirit, Hawaiian pineapple became a mainland mainstay. For over 100 years, upside-down pineapple cake has glided up and down the popularity scale, but there’s no wonder why it is on the way up again.

• Serve pineapple cake warm with vanilla ice cream for a fabulous combination.
• Garnish cake slices with whipped cream, lightly toasted coconut shreds, and a cherry on top.
• Enjoy pineapple cake chilled at a backyard BBQ or picnic.
• Sprinkle with flavorful toasted almond slivers for a crunchy texture contrast.