Pineapple Upside Down Cake Recipe

I worked SO hard on perfecting this pineapple upside down cake. Firstly, it’s a classic dessert that never goes out of style … but I’ve always felt that it could be improved.

Some of the pineapple upside down cake recipes I’ve made were too sweet, dense, or soggy – so I set out on a quest to make the most fantastic recipe I could fathom. 

And I did just that. It’s a soft pineapple cake with the best flavor!! The caramelized fruit on top melts into the soft crumb, keeping the cake tender and perfectly moist.

It has that classic cake your grandma made vibe, but elevated with richer flavor and an even softer texture. 

Serve it warm with a scoop of vanilla ice cream and you’ll understand why this one stays in heavy rotation in my kitchen.

It’s simple, nostalgic, and absolutely delicious.. which is really my favorite combination. 🙂

Why You Need To Make This Recipe!

• This is a fantastic recipe for beginners and seasoned bakers alike because it’s simple, fuss-free, and always a crowd-pleaser.
• It flips out beautifully every single time, giving you that dramatic reveal moment that makes you feel like a baking star.
• It’s a classic cake that fits every season! cozy enough for fall, breezy enough for summer, and perfect for any holiday table.

Key Ingredients

(full list of ingredients can be found in the recipe card)

• Canned pineapple rings are easiest to use for the pineapple topping. You can use fresh but you’ll need to cook them first.
• Maraschino Cherries are added for the cutest pop of color. Save some of the juice for the cake, too!
• Cake flour is how you get that soft, plush, tender crumb. Cake flour is milled extra fine with a lower protein content, which means less gluten formation aka a fluffier, melt-in-your-mouth bite. I use this for my blueberry upside down cake, too! 
• Room-temperature butter and vegetable oil add flavor, richness, and moisture. Butter traps air during creaming (hello, lift!), while oil stays liquid even when the cake cools, keeping every bite soft and silky.
  Light Brown sugar melts into that sticky, caramelized pineapple layer. Granulated sugar sweetens the cake and helps with proper browning. 
• Large eggs emulsify your batter, add richness, and help the whole cake set so it doesn’t collapse under the fruit’s moisture.
• Rum extract add just a little tropical touch.
• Pineapple emulsion (optional!) adds an extra pop of pineapple flavor. Totally optional, but it does turn the flavor dial up to 10. I also use this in my pineapple pound cake and it adds so much flavor!
• Buttermilk is the queen of moisture and tenderness. It adds tang balances the sweetness. It also reacts with baking powder for a fluffier, higher, tastier.
• Pineapple juice and maraschino cherry juice add flavor, and natural sugars that caramelize beautifully. They also reinforce that tropical vibe without drowning the batter.
• Crushed pineapples add moisture and a little texture. Just make sure to drain them!

How To Make Pineapple Upside Down Cake 

Prep: Preheat the oven to 325 degrees F. Brush a 9×3 inch cake pan with butter, brushing the entire pan to ensure all of it is coated. Line the bottom and sides of the pan with parchment paper. 

Dry The Pineapple Rings and Make the Batter

Step 1: Place sliced pineapple rings onto a few paper towels and use an additional paper towel on top to gently press into the pineapples to remove as much moisture as possible. Do the same with the maraschino cherries on another paper towel.

Step 2: Now make the cake batter. Combine cake flour, baking powder, nutmeg, and kosher salt in a large bowl and whisk together. Set aside. 

Step 3: In a separate bowl, combine butter, vegetable oil, sugar, and brown sugar. Use an electric hand mixer to beat together for 2 minutes, until fully combined and pale in color. Add in the eggs, vanilla extract, rum extract, and pineapple emulsion. Continue to mix for about 1 minute, until combined, then add in the drained crushed pineapples. 

Step 4: Add half of the dry ingredients and mix. Pour in the wet ingredients – buttermilk, pineapple juice, and maraschino cherry juice, and mix until combined, about 30 seconds. Then, add the remainder of the dry ingredients.

Assemble the Pineapple Upside Down Cake

Step 5: Pour melted butter onto the bottom of the cake pan and sprinkle dark brown sugar on top.

Step 6: Place the pineapples on top of the sugar/butter mixture, then add the maraschino cherries in the center of the pineapples and the spaces around them. For the last three pineapple slices, cut them in half and place them against the sides of the pan. 

Step 6: Pour the cake batter into the pan, gently so as to not disturb the pineapples, and smooth into an even layer. Bake for 50-60 minutes, until a toothpick comes out with just a few moist crumbs. Allow the cake to cool in the pan for 8-10 minutes. 

Recipe Note: if the cake has developed a dome in the center, just before turning over, cut the dome so that the cake is one even layer. Then turn over onto the wire rack or serving platter to cool. The dome can cause the cake to crack and not set properly.