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Pineapple Upside-down Cake is a retro classic! This delightful and delicious dessert features a soft, buttery vanilla cake infused with sweet pineapple juice and gooey caramelized brown sugar, then finished with canned pineapple rings and maraschino cherries. It’s a cake for all occasions and celebrations!
If my grandmother made a cake, it was a pineapple upside-down cake. It’s the only homemade cake recipe I can recall from my childhood (on my dad’s side). Truthfully, I didn’t care for it then (sorry, Grandma), but I’ve come around.
Easy Pineapple Upside Down Cake
To make this pineapple upside-down cake, pineapple slices and maraschino cherries are placed in a gooey, sticky mixture of melted butter and brown sugar at the bottom of a cake pan. The buttery vanilla cake batter is poured over the top and baked. After baking, the pan is inverted (aka flipped upside down) and turned out of the pan, revealing the rich, sugary topping of caramelized pineapples and cherries.
Yummy, yes? Let’s make it.
Best Pan for Pineapple Upside Down Cake
You have several options here, all of which are equally great. The most popular choice is an 8-inch or 9-inch round cake pan. round pan works nicely since it allows the pineapple rings to fit snugly together. Alternatively, you can use a large, well-seasoned cast iron skillet or a square or rectangular baking dish.
Most importantly, however, use a pan that is at least 2 inches deep and grease the pan’s bottom thoroughly (or line it with parchment paper) to ensure the cake releases easily when flipped.
Key Ingredients
Find the printable recipe with measurements in the recipe card below.
- Butter: If you have salted and unsalted butter available, I recommend using unsalted butter for the cake batter and salted butter for the caramel-like topping. If not, use your preference. I prefer salted butter.
- Sugar: We will need both granulated sugar and brown sugar. The granulated sugar will sweeten the cake, while the brown sugar will mix with the melted butter to make a sticky caramel-like topping.
- Eggs plus egg yolks: Eggs are a binder, helping give the cake its light, airy texture.
- Vegetable oil: To keep the cake moist.
- Vanilla extract: To make it a vanilla cake!
- Milk: For moisture. Tip: For more pineapple flavor, swap half of the milk for pineapple juice.
- Dry ingredients: All-purpose flour, cornstarch, baking powder, and salt.
- Pineapple slices: Canned pineapple rings are most often used because they’re convenient and sliced in even, perfect slices. However, you may also use fresh pineapple if preferred.
- Maraschino cherries: The cherries are placed in the center of the pineapple rings for color and sweetness. They are primarily used for decoration; omit them if desired.
How to Make Pineapple Upside Down Cake
1. Preheat the oven to 350 degrees Fahrenheit and spray a 9×13 baking dish or 9-inch round cake pan with nonstick spray. Set aside for later.
2. Prepare the cake batter: In a medium bowl, sift together the dry ingredients (all-purpose flour, cornstarch, baking powder, and salt). In a separate bowl, cream the butter and sugar until light and fluffy, about 2 minutes. Add the eggs and egg yolks, followed by the oil and vanilla extract, mixing between each addition until just combined.
Add the flour in three additions, alternating with the milk between each addition. It will look like this: 1/3 flour, mix, 1/2 milk, mix, 1/3 flour, mix, 1/2 milk, mix, 1/3 flour, mix.
3. Prepare the topping: Melt the remaining stick of butter in a microwave-safe bowl and pour it into the prepared baking dish. Sprinkle with the brown sugar, then arrange the pineapple rings and cherries as desired (you can copy how I arranged mine or get creative with different patterns).
4. Pour the batter over the topping: Carefully pour the cake batter over the topping in an even layer.
5. Bake: Transfer to the oven and bake for 35-45 minutes or until a toothpick inserted in the middle comes out clean. Remove from the oven and allow the cake to cool for at least 30 minutes before inverting. This allows time for the topping to set.
6. Flip: Carefully slide a sharp knife around the edges of the cake to loosen any stuck bits. Place a shallow baking pan, cutting board, or serving tray upside down on top of the cake pan. Then, tightly grab both sides, flip the cake upside down, and gently tap the pan to release the cake.
7. Serve: Slice and serve with homemade whipped cream, Cool Whip, or ice cream, if desired.
Can I Make Pineapple Upside Down Cake With Cake Mix
Yes. Using cake mix definitely simplifies the process. To make your cake with cake mix, follow the instructions as outlined, but swap the cake ingredients for your favorite cake mix! Add extra moisture by replacing water with pineapple juice and add flavor with a teaspoon of vanilla extract.
Helpful Cooking Tools For This Recipe
Check out all of my kitchen essentials. (Amazon affiliate links*)
- Glass mixing bowls
- Measuring cups and spoons
- Hand Mixer
- Round cake pan, Baking dish, or Cast iron skillet
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More Delicious Desserts
- Sweet Potato Pie Recipe
- Watergate Salad
- Pineapple Fluff
- Lemon Bars
- Carrot Sheet Cake Recipe with Cream Cheese Frosting
- Lemon Raspberry Cookies
BROWSE all of my DESSERT RECIPES!
Pineapple Upside Down Cake Recipe
Ingredients
For the Cake
- 1 stick butter, softened
- 1 cup granulated sugar
- 2 eggs, at room temperature
- 2 egg yolks, at room temperature
- 2 tablespoon vegetable oil
- 1 tablespoon vanilla
- 1 cup milk, at room temperature
- 2 cups all-purpose flour
- 2 tablespoon cornstarch
- 2 teaspoon baking powder
- ¼ teaspoon salt
For the Topping
- 1 stick butter, melted
- 1 cup brown sugar, packed
- 2 (20-ounce) cans pineapple rings (or 12 slices), drained
- 1 cup maraschino cherries
Instructions
- Preheat the oven to 350 degrees Fahrenheit and spray a 9×13 baking dish or 9-inch round cake pan with nonstick spray. Set aside for later.
- In a medium bowl, sift together the dry ingredients (all-purpose flour, cornstarch, baking powder, and salt). In a separate bowl, cream the butter and sugar until light and fluffy, about 2 minutes. Add the eggs and egg yolks, followed by the oil and vanilla extract, mixing between each addition until just combined.
- Add the flour in three additions, alternating with the milk between each addition. It will look like this: 1/3 flour, mix, 1/2 milk, mix, 1/3 flour, mix, 1/2 milk, mix, 1/3 flour, mix.
- Melt the remaining stick of butter in a microwave-safe bowl and pour it into the prepared baking dish. Sprinkle with the brown sugar, then arrange the pineapple rings and cherries as desired (you can copy how I arranged mine or get creative with different patterns).
- Carefully pour the cake batter over the topping in an even layer.
- Transfer to the oven and bake for 35-45 minutes or until a toothpick inserted in the middle comes out clean.
- Remove the cake from the oven and allow it to cool for at least 30 minutes before inverting. This allows time for the topping to set.
- Carefully slide a sharp knife around the edges of the cake to loosen any stuck bits. Place a shallow baking pan, cutting board, or serving tray upside down on top of the cake pan. Then, tightly grab both sides, flip the cake upside down, and gently tap the pan to release the cake.
- Slice and serve with homemade whipped cream, Cool Whip, or ice cream, if desired.
Notes
- Optional: Combine ¼ cup of pineapple juice with ¾ cup of milk (rather than a full cup of milk) for the cake batter.
- Fresh pineapple may be used in place of canned pineapple, and maraschino cherries may be omitted.
- Leftover pineapple upside-down cake can be stored at room temperature for up to 1-2 days. Wrap in plastic wrap or store in an airtight container. Refrigeration is recommended for longer storage (up to 3-4 days).
Nutrition
Nutrition information is automatically calculated, so should only be used as an approximation.
