Pineapple Upside Down Cake

March 2, 2019

The only Pineapple Upside Down Cake recipe 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!

Slice of Pineapple Upside Down Cake on a white serving plate. Cake is topped with fresh pineapple slices and decorated with whipped cream and a maraschino cherry.

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!

Overhead image of Pineapple Upside Down Cake showing rows of pineapple chunks. Cake is decorated with swirls of whipped cream. Along the edge of the cake are pink flowers and pineapple leaves for decoration.

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.

Ingredients needed to make pineapple upside down cake shown here including fresh pineapple, flour, brown and white sugar, butter, eggs, baking powder, salt, milk, cream and maraschino cherries.

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.

Showing how to make Pineapple Upside Down Cake. Spreading brown sugar butter topping into a 9-inch cake pan.

  • 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).

Adding fresh pineapple chunks over brown sugar layer in cake pan.

  • 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.

Adding homemade cake batter over pineapple layer in cake pan.

  • 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.

Whole Pineapple Upside Down Cake shown after baking and inverting onto marble platter.

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 pineapplemake 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.

Cutting a slice of Pineapple Upside Down Cake

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!

Three slices of Pineapple Upside Down Cake on individual white ruffled dessert plates.

More Classic Cake Recipes You’ll Love!

Pineapple Upside Down Cake

The best pineapple upside down cake! Made with a tender homemade vanilla cake, bright fresh pineapple and decorated with fluffy whipped cream and cherries for a classic simple finish.

Servings: 10
Prep Time 30 minutes
Cook Time 35 minutes
Total Time 1 hour 5 minutes

Ingredients

  • 1/4 cup unsalted butter, melted
  • 1/2 cup (100g) packed light brown sugar
  • 2 cups (300g) fresh cubed pineapple, cut into pieces about 1/2-inch thick
  • 1 1/3 cups (192g) all-purpose flour (scoop and level)
  • 1 1/2 tsp baking powder
  • 1/4 tsp salt
  • 3/4 cup (150g) granulated sugar
  • 1/2 cup (113g) unsalted butter, softened
  • 2 large eggs
  • 1 1/2 tsp vanilla extract
  • 2/3 milk (anything but skim)
  • Sweetened whipped cream for serving (optional)
  • Maraschino cherries or fresh cherries for serving (optional)

Instructions

  1. Preheat oven to 350 degrees. Spray a 9 by 2-inch cake pan with non-stick cooking spray.

  2. 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.

  3. Spread pineapple chunks over brown sugar layer in rows (leave about 1/4-inch between pieces for cake batter to fill in). Set aside.

  4. In a mixing bowl whisk together flour, baking powder, and salt, set aside.

  5. In the bowl of an electric stand mixer (or in a mixing bowl using an electric hand mixer) whip together granulated sugar and 1/2 cup softened butter until pale and fluffy.

  6. Add in one egg and mix until combined, then mix in second egg and vanilla.

  7. Add 1/3 of the flour mixture and mix just until combined, then mix in 1/3 cup milk blending just until combined. Mix in another 1/3 cup flour then mix in remaining 1/3 cup milk. Mix in last 1/3 cup flour.

  8. Pour and spread batter evenly over pineapple layer. Bake in preheated oven until toothpick inserted into center comes out clean, about 35 - 40 minutes.

  9. 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.

  10. If topping with whipped cream let cool completely. Garnish with cherries if desired.

Recipe Notes

Whipped cream and cherries not including in nutritional information.

Nutrition Facts
Pineapple Upside Down Cake
Amount Per Serving
Calories 325 Calories from Fat 135
% Daily Value*
Fat 15g23%
Saturated Fat 9g56%
Cholesterol 70mg23%
Sodium 84mg4%
Potassium 176mg5%
Carbohydrates 44g15%
Sugar 28g31%
Protein 3g6%
Vitamin A 505IU10%
Vitamin C 14.4mg17%
Calcium 75mg8%
Iron 1.3mg7%
* Percent Daily Values are based on a 2000 calorie diet.
Course: Dessert
Cuisine: American
Keyword: Pineapple Upside Down Cake
Author: Jaclyn