Golden caramelized pineapple and a soft, buttery cake—this pineapple upside-down cake is as beautiful as it is delicious!

a slice of pineapple upside-down cake topped with whipped cream and a maraschino cherry; more cake and a pineapple in the background

Pineapple upside-down cake is a timeless dessert known for its beautiful caramelized pineapple topping and soft, buttery cake. With a perfect balance of sweetness and a hint of tang from the pineapple, this cake is a delightful treat for any occasion. Whether you’re baking it for a family gathering or simply craving a nostalgic classic, this recipe is sure to impress! Plus, it’s a fantastic make-ahead dessert that tastes just as good the next day.

Why You’ll Love This Pineapple Upside-Down Cake Recipe

Classic and nostalgic. A retro favorite that never goes out of style.
Beautiful presentation. The caramelized pineapple rings and cherries make for a stunning dessert.
Perfectly moist cake. The combination of pineapple juice and butter ensures a soft, tender crumb.
Simple ingredients. No need for fancy ingredients; everything is easy to find.

overhead view of ingredients for pineapple upside-down cake

Key Ingredients

Pineapple rings and cherries – The signature look and flavor of this cake. Canned pineapple works well, but fresh pineapple can be used for a brighter flavor. If using fresh, slice it to a similar thickness as canned rings for even baking.
Brown sugar and butter – Create a rich caramel topping.
All-purpose flour – Provides structure to the cake. As always, measure accurately using a digital kitchen scale or the spoon and sweep method.
Pineapple juice – Enhances the tropical flavor and keeps the cake moist.
Vanilla extract – Adds warmth and depth of flavor.

How to Make Pineapple Upside-Down Cake

overhead view of butter and brown sugar mixture spread in the bottom of a cake pan — Make the topping.

overhead view of pineapple rings and maraschino cherries on top of brown sugar mixture in a cake pan — Make the topping.

Prepare the topping. Mix melted butter and brown sugar, then spread it in the cake pan. Arrange the pineapple slices and cherries.
Make the cake batter. Cream butter and sugar, add eggs and vanilla, then alternate adding dry ingredients and the milk-pineapple juice mixture.

overhead view of egg added to creamed butter and sugar — Add each egg, followed by the vanilla.

overhead view of dry ingredients added to cake batter — Add each egg, followed by the vanilla.

Bake the cake. Pour the batter over the topping and bake until golden and set.
Invert and serve. Let it cool slightly, then flip onto a plate to reveal the beautiful caramelized topping!

overhead view of pineapple upside-down cake batter in a cake pan ready to go into the oven — Spread evenly over topping.

overhead view of freshly baked pineapple upside-down cake in a cake pan on a wire rack — Spread evenly over topping.

How to Remove the Cake from the Pan

Flipping the cake can feel intimidating, but with the right approach, it’s easy!

Let the cake rest for 10-15 minutes after baking. This allows the topping to set slightly while still being warm enough to release easily.
Run a knife around the edges to loosen any stuck areas before flipping.
Place a serving plate over the cake pan and carefully but confidently flip it over in one smooth motion. (You can use the cooling rack if needed to avoid touching the warm pan.)
Gently lift the pan off. If any pineapple sticks, use a spatula to reposition it.
Let the cake cool slightly before slicing and serving for the best texture.

pineapple upside-down cake on a serving plate; two pineapples and a bowl of maraschino cherries partially visible in the background

Tips for Success

Use a nonstick cake pan. This will help ensure the cake releases easily.
Optional parchment paper lining. For extra insurance against sticking, you can cut a round of parchment paper to fit the bottom of the pan before adding the butter-sugar mixture.
Grease the sides of the pan. Even though the topping has butter, greasing the sides helps prevent sticking.
Using fresh pineapple? If using fresh pineapple, you can extract juice by pressing the fruit through a fine mesh strainer or blending and straining it. Fresh juice will add extra brightness to the cake.
Preventing a soggy cake bottom. If using canned pineapple, lightly pat the rings with paper towels to remove some of the moisture before placing them in the pan. For fresh pineapple, let the slices drain on a paper towel for a few minutes to remove excess moisture.
Use room temperature ingredients. Butter (which should be softened), eggs, and milk blend more easily when at room temperature, resulting in a smoother batter and better texture.
Don’t over-mix the batter. This keeps the cake soft and tender.
Let it cool slightly before inverting. About 10-15 minutes allows the topping to set without sticking. (See above for more tips for removing the cake from the pan.)
Serve warm or at room temperature. Best enjoyed fresh with a dollop of whipped cream or a scoop of vanilla ice cream!

a slice of pineapple upside-down cake on a cake server with the remaining cake behind it

Storage

Room temperature: Store tightly covered for up to 2 days.
Refrigerator: Keeps well for up to 4 days in an airtight container. Bring to room temperature before serving, or warm individual slices in the microwave for about 10-15 seconds.
Freezer: Wrap slices in plastic wrap and place in an airtight, freezer-safe container or resealable bag. Freeze for up to 2 months. Thaw at room temperature before serving.

More Nostalgic Desserts

Banana Pudding

Sour Cream Pound Cake

Chocolate Cobbler

a slice of pineapple upside-down cake on a white plate with more cake and a bowl of maraschino cherries in the background

pineapple upside-down cake on a cake plate with a slice missing; two pineapples and a bowl of maraschino cherries partially visible in the background

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