Pineapple upside-down cake has been a longtime family favorite in my house. My mom first got the recipe from a a cookbook when I was a kid, and she played with it so many times I lost track.

I’ve continued the tradition, tweaking it to fit my tastes with a few different ingredients than what it started with. Now, this is the cake half my family asks me to make for birthday cakes instead of a more traditional one.

A person wearing glasses sits at a table behind a festive pineapple upside down cake with lit candles.

I know one of the first things my mom did was change it from the smaller 8×8 pan to a 9×13 pan instead. That simple swap makes it perfect for feeding a crowd, whether it’s a family dinner, a potluck, or just a weekend treat.

PS I also make individual pineapple upside down cakes that are just as delicious and perfect for a dinner party or if you want to enjoy one and then freeze the rest. I love single serving desserts!

Some links in this article are affiliate links that may earn me a commission if you purchase through them.

Can I use buttermilk in this cake?

Yes, and my mom’s version of this recipe used buttermilk, but I feel like I buy buttermilk and then have half of it go bad every time unless I make a ton of Irish soda bread.

Instead, I use a mix of plain whole milk yogurt and regular milk because I tend to have those on hand, and they don’t go bad since I use them all the time. If you want to use buttermilk, use one cup of buttermilk in place of the yogurt and regular milk.

What type of milk should I use?

Whole milk works best for this cake rather than skim or 2% because it gives the batter a rich, creamy flavor. Using lower-fat milk can make the cake a little less tender and the topping less moist than you want.

How many pineapple rings should I use for this recipe?

They’ve reduced the number of pineapple rings in a can, which might come as a surprise to some. There are now only 10 rings per can instead of 12, so you may need to adjust the amount or plan ahead when following the recipe.

I usually buy two cans and let my kids enjoy the extra pineapple, but sometimes I forget. When that happens, I cut two of the rings in half and place them carefully on the cake to fill in the gaps and make it look full and evenly arranged.

How many maraschino cherries should I use on this cake?

Technically, the recipe calls for just 12 maraschino cherries. That’s the standard amount, but it’s really up to you and your taste preferences.

My family loooooooves maraschino cherries, so I tend to place them in every open space on the cake after arranging the pineapple rings. Feel free to use as many as you like, or stick with the prescribed 12 if you prefer a simpler look.

Sliced pineapple rings and red cherries arranged in rows in a metal baking pan, ready to be transformed into a classic pineapple upside down cake.

Do I need to grease the pan for this cake?

You don’t need to grease your pan for this cake because it releases so easily on its own. The butter and sugar mixture on the bottom ensures that it releases without any additional interference.

I run a quick edge around the cake just before flipping it to make sure it comes out cleanly. This little step takes just seconds and helps keep the caramelized pineapple and cherries looking flawless on top.

How to Make Pineapple Upside Down Cake

Turn your oven to 350 degrees. Cut one stick of butter into small pieces and place them evenly in your 9×13-inch pan.

Put the pan in the oven while it preheats to melt the butter. As it does that, prepare the cake batter.

Once the butter is fully melted, sprinkle the brown sugar evenly over the melted butter. Arrange the pineapple rings on top of the sugar mixture, making sure they’re spaced nicely, and place a maraschino cherry in the center of each pineapple ring.

A rectangular metal tray containing a layer of crystallized brown sugar, reminiscent of the glossy topping on a pineapple upside down cake, with uneven clusters and a caramelized surface.

While the butter melts, cream softened butter, granulated sugar, and brown sugar in a mixing bowl until the mixture is fluffy and comes back together. Add eggs one at a time, beating after each, then mix in vanilla and almond extracts.

In a separate bowl, whisk the flour, baking powder, baking soda, and salt. Use a liquid measuring cup to mix the yogurt, milk, and pineapple juice.

Alternate adding dry ingredients and yogurt mixture to the creamed butter, beginning and ending with the dry ingredients. Mix until just combined, being sure that you don’t overmix.

A close-up of thick, light brown pineapple upside down cake batter being mixed in a metal bowl with a purple spatula.

Carefully spread the batter over the pineapple and cherry layer. Drop spoonfuls of batter across the surface, then gently spread it with a spatula, rather than pouring it all in the center, to avoid disturbing the fruit.

Cake batter being spread over a layer of pineapple rings and maraschino cherries in a metal baking pan, preparing a classic pineapple upside down cake.

Bake the cake for 40 to 45 minutes, or until the top turns golden brown and a toothpick inserted in the center comes out clean. Watch the cake closely near the end to prevent overbrowning and ensure it bakes evenly.

A knife is being used to cut into a rectangular pineapple upside down cake in a metal baking pan on a granite countertop.

Let the cake cool in the pan for 10–15 minutes. Run a straight edge around the cake, then place a large platter or tray over the pan and invert quickly, but carefully and gently remove the 9×13 pan.