Pineapple Upside Down Cake

This pineapple upside down cake has a tender, velvety crumb with a buttery, vanilla flavor. The topping is a slightly gooey, caramel number with a beautiful mosaic of pineapple rings and maraschino cherries topping. It’s a classic that does not disappoint!

This cake has been a favorite of mine since I was 5 years old! My grandma used to make Sunday suppers, especially for me! This is her recipe with one slight change. I use cake flour instead of all-purpose flour.

Pineapple makes such amazing desserts, I just absolutely love them! I hope you’ll try my pineapple sunshine cake, pineapple delight, cherry pineapple dump cake, and pineapple sheet cake next!

Pineapple Upside Down Cake Ingredients

Topping

• Brown Sugar: You can use either light or dark brown sugar.
• Butter: I use unsalted butter.
• Vanilla: Only use pure vanilla extract. The flavor is significantly better than imitation vanilla.
• Pineapple Slices: Be sure that you pat them dry, well,  before adding them to the topping.
• Maraschino Cherries: Make the perfect red garnish. If you don’t have them, you could substitute pecan or walnut halves.

Cake

• Cake Flour: Cake flour gives this cake a velvety crumb. All-purpose flour will work but the cake won’t be quite a s tender.
• Baking Powder + Baking Soda: Both leavening agents are used in this recipe to create the perfect texture.
• Salt: Its main function in this recipe is to enhance the flavors in the cake.
• Butter: This recipe has been developed using unsalted butter.
• Sugar: Granulated sugar.
• Eggs: Large eggs at room temperature.
• Buttermilk: Well shaken and at room temperature.
• Vanilla Extract: Use pure vanilla extract.

Tips

Why Is My Caramelized Pineapple Upside-Down Cake Soggy?

If your cake is soggy, it’s likely that you didn’t dry the pineapple well enough, or the cake wasn’t baked enough.

Storing + Freezing + Make-Ahead

• Storing: The best way to store pineapple upside-down cake is to loosely cover it with plastic wrap. Ideally, it’s then best to store it in an airtight container, like a plastic cake carrier with a locking top, in the fridge.
• How Long Can You Keep This In The Fridge? Cakes can be kept in the fridge for 3-4 days.
• Can You Freeze This? Yes, completely cool the pineapple upside down cake. Place the cake on a baking sheet uncovered and freeze it. When the cake is frozen, hotel wrap, here’s how then slide it into a freezer-safe bag. Sometimes, I like to cut mine and freeze it in individual slices so I can just pull out a little at a time. It’ll last in the freezer for 3 months.
• Make-Ahead Tips: This is best to serve freshly baked but you can bake this ahead and store it in the fridge or in the freezer.
• Food Safety: If you’d like more info on cake food safety check out this link.

How To Make Pineapple Upside Down Cake

1. Make Topping: Melt butter in a 9-inch cast iron skillet.
2. Add brown sugar and whisk until the sugar dissolves and the syrup boils and is bubbly.
3. Arrange the pineapple slices evenly on the sugar mixture.
4. Add the cherries to the inside of the pineapple rings then wherever there’s a gap.
5. Make The Cake: Cream together butter and sugar until light and fluffy. Add eggs one at a time.
6. Add the flour mixture and buttermilk alternately, beginning and ending with the flour mixture. Stir in the vanilla.
7. Gently spoon the batter evenly over the pineapple slices. Bake. Let it cool.
8. Invert the cake onto a cake plate.

***See Full Instructions Below.

More Fruity Cakes You’ll Love

If your family loves cake as much as mine, check out all my cake recipes! Everyone in the family has their favorites, which ones will be yours? I’d love to hear all about which ones your family loves!

• Lemon Buttermilk Cake
• Strawberry Cake
• Apple Bundt Cake
• Heaven On Earth Cake
• Blueberry Pound Cake
• Pig Pickin Cake
• Pineapple Dump Cake

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Pineapple Upside Down Cake

This pineapple upside down cake has a tender, velvety crumb with a buttery, vanilla flavor, and is topped with pretty pineapple rings and maraschino cherries.

Prep Time20 minutes mins

Cook Time35 minutes mins

Total Time55 minutes mins

Servings: 6 slices

Author: Kathleen

Ingredients

Topping:

• 1 cup brown sugar, firmly packed
• 6 tablespoons butter
• 1/2 teaspoon vanilla extract
• 1 (20-ounce) can pineapple slices, drained
• 15-20 maraschino cherries, stems removed

Cake:

• 1 cup cake flour
• 1 cup all-purpose flour
• 1 teaspoon baking powder
• 1 teaspoon baking soda
• 1/4 teaspoon salt
• 1/2 cup butter, softened
• 1 cup sugar
• 2 large eggs at room temperature
• 1 cup buttermilk, well shaken, at room temperature
• 2 teaspoons vanilla extract

Instructions

Make Topping:

• In a 9-inch cast iron pan set over medium heat, melt 6 tablespoons of butter. Add 1 cup of the brown sugar and whisk for about 2 minutes, or until the sugar dissolves and the syrup boils and bubbles. Add vanilla (1/2 teaspoon) after removing it from the heat.
  
• Pat the pineapple (1 can) very dry between several thicknesses of paper towel and carefully arrange it evenly on the sugar mixture. (Remember skillet is still hot!)
  
• Add the cherries (15-20) to the inside of the pineapple rings then wherever there’s a gap. 
  
• Adjust oven rack to center position. Preheat the oven to 375°F (191°C).

Make Cake:

• In a medium, mixing bowl, whisk together both flours (1 cup cake flour + 1 cup all-purpose flour), baking powder (1 teaspoon), baking soda (1 teaspoon), and salt (1/4 teaspoon); set aside.
• In a large mixing bowl, using a hand-held electric mixer, cream together butter (1/2 cup) and sugar (1 cup) on medium speed until light and fluffy, about 3 minutes.
  
• Add eggs (2) one at a time, beating just until the yolk disappears.
• Add the flour mixture and buttermilk (1 cup) alternately, beginning and ending with the flour mixture, with the mixer on low, beating just until combined. Stir in the vanilla (2 teaspoons).
  
• Gently spoon the batter evenly over the pineapple slices. Bake in preheated oven until golden brown and a toothpick inserted into the center of the cake comes out clean, 35 to 40 minutes.
  
• Cool the cake in the skillet on a wire rack for 4 minutes only.
• Remove the cake from the oven and cool on a wire rack for 4 minutes. Run a butter knife around the edge of the skillet and, wearing oven mitts and working quickly, invert the cake onto a cake plate, keeping the plate and skillet firmly pressed together. 
• Carefully lift the skillet off the cake and replace any fruit stuck to the bottom of the skillet, if necessary. Serve warm or at room temperature.

Fans Also Made:

• 
  Grandma's Fruit Cocktail Cake Recipe
• 
  Peach Bourbon Upside Down Cake
• 
  Pineapple Pound Cake
• 
  Rum Pineapple Upside Down Cake

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Notes

1. Cast Iron Skillet: The cast iron skillet is perfect to make this type of cake. This recipe starts on the stovetop and then is baked in the oven. Cast iron absorbs heat and holds it, so it’s perfect when you use both types of cooking and baking sources.
2. Cake Pan: Yes, you can this cake in a 9-inch cake pan. Make the brown sugar topping in a saucepan, following the instructions above
3. Pineapple Chunks: If you’d prefer, or simply happen to have a can of pineapple chunks or tidbits, feel free to use them instead. Follow the instructions for drying the pineapple rings and do so for the chunks.
4. Dry The Fruit: drain the pineapples very well.

© Gonna Want Seconds. Content and photographs are copyright protected. Sharing of this recipe is both encouraged and appreciated. Copying and/or pasting full recipes to any social media/website/blog is strictly prohibited.

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