Pineapple Upside Down Cake Recipe - Cooking Classy (2024)

The only Pineapple Upside Down Cakerecipe you’ll ever need! Made with a topping of fresh pineapple pieces coated in a sweet buttery, brown sugar topping. Underneath lies a tender homemade vanilla cake, and atop it’s finished with fluffy whipped cream and colorful maraschino cherries. It’s a classic dessert that’s destined to impress!

The Best From Scratch Pineapple Upside Down Cake

I’ve tried plenty of pineapple upside down cakes and this one is by far my favorite. It doesn’t use any cake mix, it’s all about being made from scratch. And the best part is the fresh pineapple!

Most pineapple upside down cakes use canned pineapple and canned pineapple really lacks flavor compared to the fresh. Once you try it this way you’ll never look back.

This cake is perfect served with the fluffy whipped cream or pair it with a scoop of rich vanilla bean ice cream.

And doesn’t something about it just have spring written all over it? Spring is just around the corner and hopefully it’s paired with a slice of this cake!

Ingredients for Pineapple Upside Down Cake

• Unsalted butter – to soften butter I like to microwave in short bursts on a plate, about 5 seconds per side and rotate until just soft not melting.
• Light brown sugar and granulated sugar– be sure not to swap the brown sugar for more white for best flavor.
• Fresh pineapple – it doesn’t have to be perfectly ripe. Mine was a bit under-ripe this time and it worked well paired with the sweetness of the sugar topping.
• All-purpose flour– when measuring the flour use the scoop and level method as noted in the recipe, or better yet use a kitchen scale.
• Baking powder – be sure your baking powder isn’t out dated so the cake rises properly. And of course don’t over-mix the batter.
• Salt – salted butter will work too, just omit the salt in the recipe.
• Eggs– no need to use room temperature eggs here, I just add them cold.
• Vanilla extract– vanilla bean paste would be a good substitute here.
• Milk – use any fat percentage but skim. Stick with cow’s milk for best results, unless there’s an allergy.

How do You Pick a Good Pineapple?

To pick a good pineapple go for one that looks plump and fresh (not brown/orange and withered). Then smell the bottom of the pineapple, it should have a distinctive pineapple scent (that sweet refreshing smell). And also I tend to favor Dole pineapple, they always seem to taste the best.

To tell when it’s ripe the color of the pineapples exterior should be yellow, it should be somewhat soft, and one of the center leaves should be easy to pull out.

But as mentioned before it doesn’t have to be perfectly ripe for this recipe, but it should be hard and super green either.

Can I Use Canned Pineapple?

Most of the time I’m able to find good fresh pineapple year round but in the event you can’t canned pineapple can be substituted. Just be sure to buy canned pineapple in juice (not syrup) and drain well.

How to Make Homemade Pineapple Upside Down Cake

• Preheat oven to 350 degrees. Spray a 9 by 2-inch cake pan with non-stick cooking spray.
• In a mixing bowl whisk together brown sugar and 1/4 cup melted butter then pour into prepared cake pan and spread into an even layer, set aside.

• Spread pineapple chunks in rows over brown sugar layer (leave about 1/4-inch between pieces for cake batter to fill in). Set aside.
• In a mixing bowl whisk together flour, baking powder, and salt, set aside.
• In the bowl of an electric stand mixer (or in a mixing bowl using an electric hand mixer) whip together granulated sugar and softened butter until pale and fluffy (this will add air bubbles to fluff up the cake).

• Mix in one egg, then mix in second egg and vanilla.
• Mix in flour in 3 additions alternating with 2 additions of milk.
• Pour and spread batter evenly over pineapple layer. Bake in preheated oven until toothpick inserted into center comes out clean, about 35 – 40 minutes.

• Remove and let cool on wire rack 10 minutes. Run an offset spatula or knife around edges to ensure it’s loosened then invert onto a serving platter.
• If topping with whipped cream let cool completely. Garnish with cherries if desired.

This Pineapple Upside Down Cake is Easier To Make Than You’d Think!

Sure we add the extra step here of cutting up a pineapple but keep in mind you don’t have to make frosting. All you need to do is make the easy brown sugar topping, prep the pineapple,make the cake batter, layer into pan and bake.

And no fancy decorating required here. The pineapple adds a pretty design all on it’s own.

How Do You Make Mini Pineapple Upside Down Cakes?

I’ve shared a recipe for perfectly cut and fun, individual Pineapple Upside Down Cupcakes HERE. And back then yes I used canned pineapple but I’d recommend you even try those with small diced fresh pineapple, it will make them even better!

More Classic Cake Recipes You’ll Love!

• Yellow Cake
• Strawberry Cake
• Chocolate Cake
• Red Velvet Cake
• Spice Cake
• Lemon Poppy Seed Cake
• Banana Cake