Pineapple Upside Down Cake (from Scratch)

A real classic! This vintage Pineapple Upside Down Cake has been a favorite for decades, we could even say it has been popular for the past century really. You’ll find this is the Best Pineapple Upside Down Cake you’ll ever make. Just one bite of this homemade pineapple upside-down cake will take you back…way back to the days of yonder. This is one of our best cake recipes you can make without a cake mix. We guarantee your gang will adore it. This recipe makes one round pineapple upside-down cake.

Growing up, I remember my mom making an easy pineapple upside-down cake using the boxed cake mix in a 9×13 pan. I always loved this cake. It’s just so sunny-happy looking … don’t you think?

I had this particular cake brought to the front of my mind again a few years ago while reading the Janet Evanovich – Stephanie Plum series of books. If you haven’t read them, and you love quirky, make you laugh love stories/mysteries, you will enjoy them. They have a little bit of everything.

Stephanie has a giant sweet tooth, and her mom can always get her to come to the house for dinner with her parents and Grandmother if she lures her with Pineapple Upside Down Cake.

That was when I decided it was time to get one on my website. The first time I made this delicious cake recipe, was back in 2015.

Why You’ll Love Pineapple Upside Down Cake

What’s not to love about this classic pineapple upside-down cake? It is truly an amazing recipe. Soft, buttery cake batter topped with sticky caramelized pineapple slices and maraschino cherries. This from-scratch homemade pineapple upside-down cake will not disappoint! Doesn’t it look fancy? We sure think so with the shiny pineapple and cherries on top. 

All About Pineapple Upside Down Cake

The upside-down pineapple cake originated in the 1920s once canned pineapple rings became available across the United States. Research tells us that a recipe contest held by the company to promote the use of canned pineapple chose a recipe for pineapple upside-down cake as the winning recipe submitted by a woman from Virginia. 

Pineapple Upside Down Cake Recipe Ingredients 

This beautiful cake is made with basic pantry ingredients that turn into the most wonderful dessert full of sweet pineapple flavor.

For the full printable recipe, scroll to the bottom of this blog post. 

All-purpose flour – this is a basic, pantry staple every kitchen should have on hand

Baking powder – another pantry staple for every kitchen

Fine salt – any kind of salt will due but I like the texture of fine salt

Unsalted butter – I prefer to bake with unsalted butter but if you only have salted butter on hand reduce the amount of salt added

Granulated sugar – another pantry staple

White vinegar – if you don’t have any white vinegar on hand, apple cider vinegar also works

Vanilla – real vanilla extract is best but imitation vanilla extract works well too 

Eggs – any kind of egg will work

Low-fat buttermilk – if you don’t have any buttermilk on hand for each 1 cup of buttermilk pour 1 tablespoon of vinegar in a measuring cup and fill with regular milk to the 1 cup mark

Brown sugar – another pantry staple, I used light brown sugar for this tasty cake!

Brandy – feel free to use apple juice if you don’t have brandy

Canned pineapple – pineapple rings are the best for this recipe – save the pineapple juice for your morning smoothie!

Maraschino cherries – these really are the best but in a pinch, you can use dried or frozen cherries.

How To Make Pineapple Upside Down Cake

PREP

Preheat the oven to 350° F. In a medium bowl, sift together the flour, baking powder, and salt. Set aside. 

MIX

In your mixer bowl, with a paddle attachment, cream together 12 tablespoons of butter, granulated sugar, vinegar, and 2 teaspoons of vanilla until fluffy. ( 3-4 minutes or so) 

Add each egg, one at a time, to the butter mixture, beating after each addition.

On low, alternately add the dry ingredients and the buttermilk in 3 batches. Scraping down the sides of the bowl with a rubber spatula, as needed.

Set the mixer to medium and beat the batter until smooth, (about 3 minutes) Set aside.

HEAT

Over medium heat, in a small saucepan or in a skillet, melt the remaining butter.

(use a saucepan if you are baking the cake in a cake pan if you are baking it in a skillet, use that – saves on dishes!)

Whisk in the remaining vanilla, the brown sugar, and brandy, until dissolved.

ARRANGE

Remove the skillet from the heat; arrange the pineapple slices on the bottom of the skillet in a single layer. Evenly arrange the cherries among the pineapple slices.

BAKE

Gently pour the cake batter over the pineapple rings and cherries.

Bake the cake until it is golden and set, about 45-50 minutes. Ovens will vary.

Test with a toothpick placed in the center. The cake is ready when the toothpick comes out clean.

Let cool for 30 minutes and invert onto a serving plate. I think I heard angels sing when I lifted the skillet to reveal its loveliness!

Love it? Pin it!

Don’t forget where you found the recipe for this perfectly tender cake! Pin it to your favorite recipe board on Pinterest before you go!

Tips & Tricks for making the best Pineapple Upside Down Cake

Have all your ingredients on hand before you start.

Drain the pineapple and cherries well.

Let the eggs and butter come to room temperature.

How to Store Pineapple Upside Down Cake

This Pineapple Upside Down Cake will last well for about two days outside of the fridge but if you want it to last longer place it in the refrigerator in an airtight container. It’ll keep for up to 5 days.

FAQs About Pineapple Upside Down Cake

What pan works best for this pineapple upside-down cake recipe? It is best to use a round cake pan or a cast-iron skillet to bake this cake.

Why is my pineapple upside down cake soggy? To reduce the risk of a soggy cake make sure to drain the pineapple and cherries well. Sometimes taking a paper towel to remove excess moisture is also helpful. 

Why is it called pineapple upside down cake? It is called a pineapple upside down cake as it is baked with the pineapple on the bottom and then inverted for serving. 

What does pineapple upside down cake taste like? This super moist cake has a rich caramel-like flavor. 

What is the meaning of pineapple upside down cake? This means that the cake was baked with the pineapple on the bottom. The cake is then inverted before serving. 

What is an upside down cake? An upside down cake is one that is flipped over so that the side that was down during baking is right side up for serving. 

Can you make a gluten free pineapple upside down cake? If you want to make this cake gluten-free use gluten-free flour like Cup4Cup or Bob’s Red Mill. 

Can you use fresh pineapple in Pineapple Upside-Down Cake? Yes! Since you are draining the pineapple to make it while using canned pineapple, fresh will work just fine.

How long do you let a pineapple upside-down cake sit upside down? Let the cake sit for at least 30 minutes before flipping it to your serving plate.

Love Pineapple? Us, too! More Pineapple Recipes to Love

Pineapple is wonderful for baking, but we also love to use it in savory recipes. Here are some more of our favorite pineapple recipes:

• Two Ingredient Pineapple Angelfood Cake (pictured above)
• Pineapple Upside Down Cake Martini
• Hawaiian BBQ Chicken Sandwiches 
• Ham Balls with Pineapple Sauce
• Pineapple Coconut Tunnel Cake
• Pineapple Pretzel Fluff

This (from scratch) Pineapple Upside Down Cake will have you reminiscing about your childhood. Its buttery sweet goodness will make you swoon! Let’s get to the recipe for this easy dessert!

4.73 from 11 votes

Print Recipe

{from scratch} Pineapple Upside Down Cake

This {from scratch} Pineapple Upside Down Cake will have you reminiscing your childhood. It's buttery sweet goodness will make you swoon!

Prep Time10 minutes mins

Cook Time50 minutes mins

Additional Time1 hour hr

Total Time2 hours hrs

Cuisine: American

Keyword: Pineapple Upside Down Cake

Servings: 12 servings

Calories: 430kcal

Author: An Affair from the Heart

Cook ModePrevent your screen from going dark

Ingredients

• 1 3/4 cups flour
• 2 teaspoon baking powder
• 1/4 teaspoon fine salt
• 1 1/3 cups unsalted butter divided
• 1 cup granulated sugar
• 1 Tablespoon white vinegar
• 3 teaspoon vanilla divided
• 3 eggs
• 1 1/3 cup low-fat buttermilk
• 10 Tablespoons brown sugar 5/8 cup
• 2 Tablespoons brandy can sub 2 Tablespoons apple juice
• 7 slices of canned pineapple
• 1 1/2 cup stemmed maraschino cherries

Instructions

• Preheat the oven to 350° F.
• In a bowl, sift together the flour, baking powder, and salt. Set aside. In your mixer bowl, cream together 12 Tablespoons of butter, granulated sugar, vinegar, and 2 teaspoons vanilla until fluffy. ( 3-4 minutes or so) Add each egg, one at a time to the butter mixture, beating after each addition. On low, alternately add the flour mixture and the buttermilk in 3 batches. Scraping down the sides of the bowl, as needed. Set mixer to medium and beat the batter until smooth, (about 3 minutes) Set aside.
• In a 10" nonstick skillet over medium-high heat, melt remaining butter. Whisk in the remaining vanilla, the brown sugar and brandy, until dissolved. Remove the skillet from the heat; arrange the pineapple slices on the bottom of the skillet. Arrange the cherries among the pineapple slices, evenly.
• Gently pour in the cake batter. Bake the cake until it is golden and set, about 45-50 minutes. Test with toothpick in center. Ovens will vary.
• Let cool for 30 minutes and invert onto a serving plate.

Nutrition

Serving: 1g | Calories: 430kcal | Carbohydrates: 54g | Protein: 5g | Fat: 22g | Saturated Fat: 13g | Polyunsaturated Fat: 8g | Cholesterol: 102mg | Sodium: 202mg | Fiber: 1g | Sugar: 38g

This recipe was originally posted on July 12, 2015. It has been updated to improve user experience and reshared on June 28, 2022.

The recipe came from A Spoonful of Thyme and was made for a group called the Secret Recipe Club, which is no longer around.