Pineapple Upside Down Cake is the ultimate throwback dessert that never goes out of style. Sweet pineapple rings and bright cherries caramelize in a buttery brown sugar glaze, creating a golden crown of fruity goodness on top of a soft, fluffy cake. It’s the kind of dessert that feels nostalgic yet timeless.
Making pineapple upside down cake is a fun blend of simple steps and delicious results. You start by arranging pineapple rings and maraschino cherries in a buttery brown sugar glaze at the bottom of your pan. Pour a soft, fluffy batter over the top, then bake until the aroma of sweet pineapple and caramel fills your kitchen. The real fun comes at the end—flipping the cake onto a plate to reveal a golden, glossy crown of fruit that looks as amazing as it tastes. Every slice delivers that perfect mix of tender cake and caramelized fruit, making it a cheerful, nostalgic dessert everyone will love.
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Check out some of our other favorite cakes: Cinnamon Roll Poke Cake, Strawberry Cheesecake Dump Cake, Banana Pudding Poke Cake, or Strawberry Earthquake Cake.
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Ingredients for Pineapple Upside Down Cake
- yellow cake mix
- pineapple slices
- pineapple juice
- brown sugar
- butter
- eggs
- cherries
- oil
FAQs
Yes! Fresh pineapple works beautifully, but slice it evenly and consider lightly cooking it in butter and brown sugar first to get that caramelized effect.
A simple yellow or butter cake batter is traditional, but you can also try a vanilla or even a light sponge cake for a softer texture.
Grease the pan well and make sure the brown sugar and butter mixture is evenly melted. Let the cake cool for 5–10 minutes before flipping to avoid breakage. Using a spatula around the edges can also help.
Yes, but it’s best to freeze slices rather than the whole cake. Wrap tightly in plastic wrap and store in a freezer-safe bag for up to 2 months. Thaw at room temperature before serving. Note: the caramel topping may become a little softer after freezing.
Top Tips
- Timing is key – Let the cake cool for 5–10 minutes before flipping—any longer and it may stick.
- Flip with flair – Use a big plate, take a breath, and go for it in one smooth motion.
- Use a sturdy platter – The caramel glaze can drip, so grab a plate or cake stand that’s a little bigger than your pan.
- Make It Ahead: This cake is perfect for making a day in advance, giving it time to become even more flavorful.
- Store cake: If you plan to eat it within 1–2 days, store the cake in an airtight container at room temperature. Keep it away from direct sunlight to preserve the caramel glaze.
- Refrigerator: For longer storage (up to 5–6 days), cover the cake tightly with plastic wrap or store in an airtight container in the fridge.
- To freeze the cake, place slices in an airtight container, and freeze for up to 3 months. Thaw in the refrigerator overnight.
How to make Pineapple Upside Down Cake
- Preheat oven to 350°F (175°C). Grease a 9x13-inch baking pan. Melt ¼ cup butter and pour it evenly into your baking dish. Sprinkle the brown sugar over the melted butter, spreading to cover the bottom.
- Arrange the pineapple slices on top of the brown sugar, then place cherries in the centers of the pineapple rings and around them.
- In a large mixing bowl, combine the cake mix, eggs, oil, and the reserved pineapple juice (or water). Mix on low speed until smooth. Gently pour the batter over the arranged pineapple and cherries.
- Bake the cake for 40–45 minutes, or until a cake tester inserted into the center comes out clean. Carefully run a knife around the edges of the pan to prevent sticking. Let the cake cool for about five minutes.
- Place a large plate or cookie sheet over the pan, then carefully invert the cake (use oven mitts, it will be hot!). Let the pan rest on top for a few minutes so the brown sugar glaze can drip down. Remove the pan, and your classic pineapple upside down cake is ready to serve!
Pineapple Upside Down Cake
Ingredients
Pineapple Layer
- ¼ cup butter, melted
- 1 cup brown sugar, packed
- 1 20 oz can pineapple rings with juice
- maraschino cherries
Cake
- 1 15.25 oz cake mix box (yellow or french vanilla)
- 3 eggs
- ½ cup canola or vegetable oil
- 1 cup pineapple juice (or water)
Instructions
- Preheat oven to 350°F (175°C). Grease a 9x13-inch baking pan.
- Melt ¼ cup butter and pour it evenly into your baking dish. Sprinkle the brown sugar over the melted butter, spreading to cover the bottom.
- Arrange the pineapple slices on top of the brown sugar, then place cherries in the centers of the pineapple rings and around them.
- In a large mixing bowl, combine the cake mix, eggs, oil, and pineapple juice (or water). Mix on low speed until smooth. Gently pour the batter over the arranged pineapple and cherries.
- Bake the cake for 40–45 minutes, or until a cake tester inserted into the center comes out clean.
- Carefully run a knife around the edges of the pan to prevent sticking. Let the cake cool for about five minutes.
- Place a large plate or cookie sheet over the pan, then carefully invert the cake (use oven mitts, it will be hot!). Let the pan rest on top for a few minutes so the brown sugar glaze can drip down.
- Remove the pan, and your classic pineapple upside down cake is ready to serve!
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