Pineapple Upside Down Cake Recipe

This homemade pineapple upside down cake is all I want to eat during the summer season. I use toasted walnuts and pistachios as a barrier between the fruit and the batter so the cake stays moist but never soggy. The pineapple is caramelized separately in butter and brown sugar, then placed on top after baking with a brandy caramel drizzle.

There is nothing like a delicious cake to finish off a tasty meal. One of my most requested recipes is pineapple upside down cake, and while I think the flavor is always there, I am not a huge fan of soggy cake and overcooked fruit. So I came up with a workaround that fixes both of those problems. If you love baking cakes like I do, my pistachio cake and my classic carrot cake are two more favorites worth trying.

Pineapple Upside Down Cake

Pineapple upside down cake has been around for generations and was originally made as a skillet cake cooked over an open flame or stove and then inverted upon serving. Before canned pineapple was invented, skillet cakes used whatever seasonal fruit was available. When the Dole company began mass-producing canned pineapple rings in the early 1900s, the pineapple version quickly became the most popular. The concept is simple: butter, sugar, and decoratively arranged pineapple go in the bottom of the pan, cake batter goes on top, and during baking the butter, sugar, and fruit juices caramelize to create a browned glaze that becomes the top when the cake is flipped.

My version is a little unorthodox. The main reason traditional pineapple upside down cakes get soggy is because the fruit is cooked right into the batter. To solve this, I create a nut barrier between the fruit and the cake. I process walnuts and pistachios in a food processor until they become a coarse meal, pack them into the bottom of a cake pan, and toast them. The cake batter goes on top of the toasted nuts and bakes for over an hour.

While the cake bakes, I caramelize fresh pineapple rings in butter and brown sugar in a separate pan, then make a quick caramel sauce with the remaining brown sugar, heavy cream, and a shot of brandy or rum. Once the cake cools, I flip it, arrange the caramelized pineapple on top, drizzle on the caramel, and place fresh cherry halves in the center of each ring.

I know you will love this cake because it is moist and rich with a toasted nut crust on top and perfectly caramelized fruit that still has texture and flavor instead of being overcooked into mush. I recommend to watch the video below for my workaround on how to make a delicious pineapple upside-down cake.

Ingredients and Substitutions

This cake has three components: the toasted nut base, a rich butter cake, and caramelized pineapple with a brandy caramel. These are all the ingredients I use:

• Pineapple – I like to use fresh pineapple for my version of pineapple upside-down cake, but you can use spiraled canned.
• Cherries – Fresh cherries are so good on this, but jarred Marciano cherries will do.
• Nuts – I like to use walnuts or pistachios.
• Flour – You’ll need all-purpose flour for this.
• Sour Cream – A good full-fat sour cream works wonders in this.
• Sugar – Granulated sugar and brown sugar are needed for the cake and caramelizing of the pineapple.
• Butter – Always use unsalted butter so you can control the salt content.
• Vanilla – A shot of good vanilla will help bring out more flavors in this recipe.
• Oil – Any neutral-flavored oil will work.
• Eggs – Whole large eggs are perfect for this.
• Leavening Agents – I used baking powder and baking soda in this recipe.
• Salt – Sea salt will help season up our cake to perfection.
• Alcohol – You can use either Brandy or rum for our caramel sauce.
• Heavy Cream – I use this to aid in the making of the caramel.

How to Make Pineapple Upside Down Cake

Prep nut base: I preheat the oven to 350 degrees. I pulse the walnuts and pistachios in a food processor about 40 to 50 times.

Toast: I add them to a 9-inch cake pan prepared with parchment paper and non-stick spray, pack them down with a spoon, and bake for 12 to 13 minutes until toasted. I let them cool in the pan.

Mix dry ingredients: I whisk together the flour, baking soda, baking powder, and salt in one bowl.

Prep wet ingredients: In a separate bowl, I whisk together the sour cream, milk, oil, and pineapple juice.

Make cream: I cream the butter and sugar in a stand mixer with the paddle attachment on high speed for 5 to 7 minutes until light and fluffy,

Add in: Then I add the vanilla and eggs one at a time on low speed.

Combine wet and dry: I alternate adding the dry and wet ingredients, beginning and ending with the dry, just until combined.

Bake the cake: I pour the batter over the toasted nut base and smooth the top with a spatula. I bake at 350 degrees for 1 hour and 15 minutes to 1 hour and 20 minutes.

Tent cake: I tent the cake with foil halfway through so the top does not get overly browned.

Caramelize the pineapple: While the cake bakes, I melt butter in a large frying pan over medium heat, add the pineapple rings, sprinkle with 1/4 cup of brown sugar, and cook for 2 to 3 minutes until slightly caramelized. I flip and cook for 1 more minute, then remove and set aside.

Make the caramel: I add the remaining 1/4 cup of brown sugar to the same pan over medium heat, add the heavy cream, and whisk until smooth. I remove from heat and whisk in the brandy or rum.

Assemble: I let the cake cool for 20 to 35 minutes, then flip it onto a serving plate so the nut base is on top.

Finish the cake: I arrange the caramelized pineapple rings on top, drizzle the caramel over everything, and place cherry halves in the center of each ring.

Serve: I slice and serve this cake and please check my serving suggestions below.

Serving Suggestions

I serve this cake at room temperature on a platter in the center of the table and a bowl of homemade whipped cream next to it is a must. The whipped cream melts into the warm caramel and pineapple and takes each bite to another level.

A good friend requested this cake for her birthday, so I happily made it for her. She took charge of the vanilla ice cream and my homemade caramel sauce to serve alongside it, and the whole thing was a total success. By the end of the party, all the guests were asking for the recipe!

Make-Ahead and Storage

Make-Ahead: I make this cake up to 1 day ahead of time.

How to Store: I cover and keep it at room temperature for up to 3 days. It keeps in the refrigerator, covered, for up to 5 days. It freezes well, covered, for up to 3 months. I thaw it in the refrigerator for 1 day before serving.

How to Reheat: I place the desired number of slices on a sheet tray lined with parchment paper and warm in the oven at 350 degrees for 4 to 5 minutes.

More Cake Recipes

• Funfetti Cake
• Carrot Cake
• Lava Cake
• Tres Leches
• Pound Cake