How to Make Pineapple Upside-Down Cake

By Grandma Sandy | August 20, 2025

Recently, I came across a House Beautiful feature, Ten Things EVERY Boomer had in their Home Growing Up. It was fun to travel memory lane.

It made me think about the foods every boomer ate growing up. Which made me yearn for a bite of pineapple upside-down cake!

Revisiting retro recipes helps to rekindle taste memories. In our home, pineapple upside-down cake was a dessert for company. Mom was always eager to try the latest food trends of her day. Dad was game, but he finally rebelled at potato chip casserole.

A collection of cookbooklets of retro recipes from the 1940s and 1950s. — **Some of my mom’s cookbooklets–I have a boxful of these priceless retro recipes.**

How Pineapple Upside-Down Cake Got Famous

Pineapple upside-down cake was known by the late 1800s, according to Dole Food Company, Inc. But it wasn’t until 1925, when the company sponsored a recipe contest, that pineapple upside-down cake became all the rage.

Sloppy Joes features ground beef in a sweet and tangy sauce, served on toasted buns.

Out of 60,000 entries submitted, 2,500 were recipes for pineapple upside-down cake! Capitalizing on the potential to create a movement, the winning entry was heavily publicized, resulting in its ubiquity in mid-20th century American kitchens.

If you’d like to make the Original Pineapple Upside-Down Cake, winner of the 1925 contest, click HERE

Pineapple in Hawaii

Hawaiian pineapples for sale at the farmers market in Hilo, Hawaii. — **Pineapples for sale at the farmers market in Hilo, Hawaii.**

Growing up in Hawaii, Dole was a looming presence in our lives. High school kids on the neighbor islands flew to Maui to work in the pineapple fields during summer vacations. Others, including my husband Steve, worked in the cannery to earn money for college.

With high labor and land costs, pineapple farming and processing have moved off the Islands. However, some smaller farms still produce pineapples, primarily for local consumption and tourism.

Grandmother and grandchild baking together. This is a good time to tell family stories about food. — **Tell family stories when you cook together with the grandkids.**

Pineapple Upside-Down Cake and Grandkids

Making pineapple upside-down cake is a project you can do with a grandchild. Since the recipe below is made with a box mix, it comes together very quickly.

Kids can help to spread the brown sugar topping in the pan, lay down the pineapple slices and maraschino cherries, and make the batter.

Crisp Grandma's Peanut Butter Cookies cool on racks.

And here are more related things you can do together:

Introduce kids to 15 cool pineapple facts.
Grow a pineapple plant in a pot.
Make a candle salad. Remember that one? Stand a peeled banana into the hole of a pineapple slice and top with a maraschino flame.
Talk to kids about what kinds of foods you grew up with and make some of the dishes together. Tell them family food stories.

Pineapple Upside-Down Cake

The Pineapple Upside-Down Cake below is recipe from Dole using yellow cake mix. Sadly my mom’s recipe is lost.

Note: in testing this recipe, I had more batter than fits in the pan; be prepared with a muffin tin to make cupcakes with any remaining batter.

Ingredients

Non-stick cooking spray
1 can (20 ounces) Dole pineapple slices in 100% pineapple juice
1/4 cup (4 tablespoons) butter, melted
2/3 cup packed light brown sugar
7 to 8 maraschino cherries
1 package (15.25 ounces) yellow cake mix, plus vegetable oil, eggs, and any other ingredients specified on box instructions

Method

Heat oven to 350 degrees F.

Spray the sides and bottom of a 9-inch cake pan with cooking spray. Drain pineapple slices; reserve 3/4 cup juice.

Mix melted butter with brown sugar and pour into a 9-inch cake pan, spreading evenly. Arrange pineapple slices on sugar mixture and place a cherry in the center of each pineapple slice, with the nicer side of the cherries face down.

Prepare cake mix according to package directions. Instead of the entire amount of water called for in the instructions, replace 3/4 cup of the water with the reserved pineapple juice. Pour batter evenly over pineapple until batter reaches 1 inch below the top of the cake pan. Make cupcakes with remaining batter.

Bake 35 to 40 minutes until a toothpick inserted in the center comes out clean.

Remove pan from oven and cool 5 minutes. Loosen edges with a thin-bladed knife and invert onto a serving platter.

Notes:

Do not let the cake cool more than 10 minutes before inverting the pan, or the brown sugar topping will harden, making it difficult to remove the cake from the pan.
If you use a smaller size box of cake mix (13.25 ounces), it may just be enough to fill the pan without any leftover batter. Just be sure to allow an inch of clearance at the top of the pan for the cake to rise.

Recipe adapted from Dole Food Company.

**A slice of pineapple upside-down cake.**

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