This Pineapple Upside-Down Cake Recipe is a timeless, nostalgic dessert, which is made with a buttery brown sugar glaze and a tender, moist cake. It’s a visually stunning yet surprisingly simple cake to make, ready in just over an hour.
Pineapple Upside-Down Cake Ingredients
- 3 tablespoons butter
- 1/2 cup light brown sugar, packed
- 9 slices canned pineapple in juice, drained
- 5 maraschino cherries
- 1 1/2 cups sifted all-purpose flour
- 2 teaspoons baking powder
- 1/4 teaspoon salt
- 1/3 cup solid vegetable shortening
- 2/3 cup granulated sugar
- 1 large egg
- 3/4 teaspoon vanilla extract
- 2/3 cup milk
How To Make Pineapple Upside-Down Cake
- Prepare the topping: Preheat the oven to 350°F (175°C). Place the butter in an 8x8x2-inch square baking pan and set it in the oven (or on the stovetop over low heat) just until melted. Remove from the heat and sprinkle the brown sugar evenly over the melted butter.
- Arrange the fruit: Arrange the 9 drained pineapple rings in a single layer on top of the sugar, making 3 neat rows. Cut the maraschino cherries in half and place one half, cut-side up, in the center of each pineapple ring. Set the pan aside.
- Combine dry ingredients: In a medium bowl, sift the flour, baking powder, and salt together. Sift a second time to ensure the leavening is well distributed and the cake is light.
- Mix the batter: In a large bowl, use an electric mixer to cream together the vegetable shortening and granulated sugar until well combined. Beat in the egg and vanilla extract.
- Finish the batter: Add the flour mixture and the milk to the creamed mixture alternately, beginning and ending with the flour mixture. Mix on low speed only until the ingredients are just combined after each addition. Do not overmix.
- Bake the cake: Carefully pour the batter over the pineapple in the pan and spread it evenly. Bake for 40 minutes. The cake is done when a toothpick inserted into the center comes out clean, or when the center springs back when lightly pressed.
- Invert and serve: Immediately run a knife around the edges of the pan. Place a serving platter on top of the pan and, using oven mitts, carefully and quickly flip them over to invert the cake. Leave the pan over the cake for a few moments to allow all the warm brown sugar syrup to drizzle down. Serve warm.

Recipe Tips
- How to ensure a perfect flip: The key is to invert the cake while it is still hot. If you let it cool in the pan, the sugar topping will harden and stick. Running a knife around the edges right after it comes out of the oven is crucial.
- How to get a tender cake: Sifting the dry ingredients twice and being careful not to overmix the batter are the secrets to a light, tender crumb. Mix only until the streaks of flour disappear.
- Room temperature ingredients: For a smoother, better-emulsified batter, use an egg and milk that are at room temperature.
- Can I use a different pan? Yes, this recipe works perfectly in a 9-inch round cake pan. You will arrange the pineapple slices in a circular pattern instead of rows.
What To Serve With Pineapple Upside-Down Cake
This cake is wonderfully moist on its own, but it’s even better with:
- A scoop of vanilla ice cream
- A dollop of freshly whipped cream
- A drizzle of heavy cream
How To Store Pineapple Upside-Down Cake
Refrigerate: Due to the fruit topping, it’s best to store this cake in the refrigerator. Cover it loosely with plastic wrap or place it in a cake carrier. It will keep for up to 4 days. It can be served chilled or gently reheated.
Pineapple Upside-Down Cake Nutrition Facts
(Approximate values per serving, assuming 9 servings)
- Calories: 360 kcal
- Protein: 4g
- Carbohydrates: 55g
- Fat: 14g
- Fiber: 1g
Nutrition information is estimated and may vary based on ingredients and cooking methods used.
FAQs
Can I use fresh pineapple instead of canned?
Yes, you can use fresh pineapple. Slice it into rings of a similar thickness to the canned variety. You may need to pat it dry to remove excess moisture before arranging it in the pan.
Can I use butter instead of vegetable shortening?
Absolutely. You can substitute the shortening with an equal amount of softened unsalted butter for a richer, more buttery cake flavor.
Why is my topping runny?
This can happen if the pineapple is not drained well enough, releasing too much liquid into the brown sugar as it bakes. Be sure to drain the pineapple slices thoroughly before arranging them in the pan.
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Pineapple Upside-Down Cake Recipe
Description
A wonderfully moist, buttery cake baked atop a layer of caramelized brown sugar, sweet pineapple rings, and cheerful maraschino cherries.
Ingredients
Instructions
- Preheat oven to 350°F (175°C). Melt butter in an 8×8-inch pan; sprinkle with brown sugar.
- Arrange pineapple slices and halved cherries on top of the sugar.
- Sift together flour, baking powder, and salt twice.
- Cream the shortening and sugar. Beat in the egg and vanilla.
- Alternately add the flour mixture and milk to the creamed mixture, ending with flour. Do not overmix.
- Pour batter over the fruit and bake for 40 minutes until a toothpick comes out clean.
- Immediately run a knife around the edges and invert the hot cake onto a serving platter.
Notes
- Invert the cake while it is hot to prevent the topping from sticking to the pan.
- For a light and tender cake, do not overmix the batter once the flour has been added.
- Ensure pineapple slices are well-drained to prevent a watery topping.
- A 9-inch round pan can be used as an alternative to the square pan.