The Best Pineapple Upside Down Cake is a timeless classic that brings nostalgia with every bite. This cake is not only visually stunning with its vibrant pineapple slices and cherries, but it also delivers a moist and flavorful experience that is hard to resist. Perfect for gatherings or just a sweet treat at home, this cake is sure to impress. Let’s dive into the details of making this delicious dessert!
Why This Recipe Works

This recipe for The Best Pineapple Upside Down Cake works wonders because it combines the sweetness of caramelized brown sugar with the tanginess of fresh pineapple. The rich texture from the buttermilk and sour cream ensures the cake remains moist, while the baking powder provides the perfect lift. The maraschino cherries add a pop of color and a hint of sweetness that ties everything together. Each ingredient plays a vital role in creating a cake that is both delightful to the eye and the palate.
What to Buy

When preparing to make The Best Pineapple Upside Down Cake, here’s what you will need:
- Unsalted butter: ½ cup for greasing and flavor.
- Light brown sugar: ¾ cup packed, for that rich caramel flavor.
- Pineapple slices: 1 can (20 ounces), the star of the show!
- Maraschino cherries: About 12, for garnishing.
- All-purpose flour: 1 cup, for the cake base.
- Granulated sugar: ½ cup, to sweeten the batter.
- Baking powder: 2 teaspoons, for leavening.
- Salt: Pinch, optional, to enhance flavor.
- Large egg: 1, for binding the ingredients.
- Buttermilk: ½ cup, or substitute with powdered buttermilk (2 tablespoons with ½ cup water).
- Sour cream: ½ cup, for moisture (plain Greek yogurt can be used as a substitute).
- Canola or vegetable oil: 3 tablespoons, for added moisture.
- Vanilla extract: 2 teaspoons, for depth of flavor.
Toolbox for This Recipe

- 9-inch round cake pan: Ideal for even baking and easy flipping.
- Mixing bowls: For combining wet and dry ingredients.
- Measuring cups and spoons: Essential for accurate ingredient measurements.
- Whisk: For mixing and incorporating air into the batter.
- Spatula: To scrape down the sides of the bowl and for folding ingredients together.
- Cooling rack: To cool the cake after baking.
Cook The Best Pineapple Upside Down Cake Like This
Step 1: Prepare the Pan
Start by preheating your oven to 350°F (175°C). Grease your 9-inch round cake pan with 2 tablespoons of unsalted butter, making sure to cover the bottom and sides well. Sprinkle the packed light brown sugar evenly over the buttered surface.
Step 2: Arrange the Pineapple and Cherries
Place the pineapple slices in a single layer over the brown sugar. Try to fit them snugly. Place a maraschino cherry in the center of each pineapple slice and any additional cherries in the gaps for a beautiful presentation.
Step 3: Mix the Wet Ingredients
In a large mixing bowl, combine the remaining ½ cup of unsalted butter (melted), granulated sugar, and the egg. Whisk until well blended. Add the buttermilk, sour cream, canola oil, and vanilla extract. Mix until smooth.
Step 4: Combine the Dry Ingredients
In a separate bowl, whisk together the all-purpose flour, baking powder, and salt. Gradually add this dry mixture to the wet ingredients, stirring gently until just combined. Be careful not to overmix; a few lumps are okay.
Step 5: Pour the Batter
Carefully pour the batter over the arranged pineapple and cherries in the cake pan, spreading it evenly with a spatula.
Step 6: Bake the Cake
Bake in the preheated oven for 35-40 minutes, or until a toothpick inserted into the center comes out clean. Keep an eye on it to ensure it doesn’t overbake.
Step 7: Cool and Flip
Once baked, remove the cake from the oven and let it cool in the pan for about 10 minutes. Carefully run a knife around the edges to loosen it, then place a plate over the pan and flip it upside down to release the cake. Gently lift the pan to reveal the beautiful pineapple topping.
Step 8: Serve and Enjoy
Allow the cake to cool completely before slicing. Serve it plain or with a dollop of whipped cream for an extra indulgent treat!
Make It Your Way
Feel free to customize The Best Pineapple Upside Down Cake to suit your taste:
- Add nuts: Chopped pecans or walnuts can add a delightful crunch.
- Spice it up: Add cinnamon or nutmeg to the batter for a warm flavor profile.
- Use different fruits: Try using peaches or cherries instead of pineapple for a twist.
- Make it a layer cake: Double the recipe and layer with frosting for a celebration cake.
Insider Tips
- Ensure your butter is at room temperature for easier mixing with the sugar and egg.
- Use fresh pineapple for an even more vibrant flavor if desired.
- Let the cake cool before flipping to avoid any topping mishaps.
- For a more intense pineapple flavor, use pineapple juice in place of buttermilk.
Save for Later: Storage Tips
The Best Pineapple Upside Down Cake can be enjoyed fresh, but if you have leftovers, here’s how to store them:
- Cover the cake with plastic wrap or aluminum foil to keep it fresh for up to 3 days at room temperature.
- For longer storage, refrigerate for up to a week. Just remember to bring it back to room temperature before serving.
- You can also freeze slices wrapped tightly in plastic wrap for up to 3 months. Thaw in the refrigerator overnight before enjoying.
Ask & Learn
Can I use fresh pineapple instead of canned?
Absolutely! Fresh pineapple will give your cake a vibrant flavor. Just slice it into rings and follow the same arrangement process as with canned pineapple.
What can I substitute for buttermilk?
You can make a quick substitute by mixing 1 tablespoon of vinegar or lemon juice with enough milk to make ½ cup. Let it sit for a few minutes before using.
How do I know when the cake is done baking?
A toothpick inserted into the center of the cake should come out clean or with a few crumbs attached. Keep an eye on the edges; they should pull away slightly from the pan.
Can I make this cake ahead of time?
Yes! You can bake the cake a day in advance. Just store it covered at room temperature and flip it over just before serving for the best presentation.
In Closing
With its delightful combination of flavors and textures, The Best Pineapple Upside Down Cake is sure to become a favorite in your household. Whether you’re serving it at a family gathering, a birthday party, or simply enjoying it with a cup of tea, this cake is a guaranteed crowd-pleaser. Happy baking!

The Best Pineapple Upside Down Cake
Ingredients
For the Cake:
- ½ cup Unsalted butter for greasing and flavor
- ¾ cup Light brown sugar packed
- 1 can (20 ounces) Pineapple slices the star of the show!
- 12 Maraschino cherries for garnishing
- 1 cup All-purpose flour for the cake base
- ½ cup Granulated sugar to sweeten the batter
- 2 teaspoons Baking powder for leavening
- 1 pinch Salt optional, to enhance flavor
- 1 Large egg for binding the ingredients
- ½ cup Buttermilk or substitute with powdered buttermilk (2 tablespoons with ½ cup water)
- ½ cup Sour cream for moisture (plain Greek yogurt can be used as a substitute)
- 3 tablespoons Canola or vegetable oil for added moisture
- 2 teaspoons Vanilla extract for depth of flavor
Instructions
Instructions
- Step 1: Prepare the Pan - Start by preheating your oven to 350°F (175°C). Grease your 9-inch round cake pan with 2 tablespoons of unsalted butter, making sure to cover the bottom and sides well. Sprinkle the packed light brown sugar evenly over the buttered surface.
- Step 2: Arrange the Pineapple and Cherries - Place the pineapple slices in a single layer over the brown sugar. Try to fit them snugly. Place a maraschino cherry in the center of each pineapple slice and any additional cherries in the gaps for a beautiful presentation.
- Step 3: Mix the Wet Ingredients - In a large mixing bowl, combine the remaining ½ cup of unsalted butter (melted), granulated sugar, and the egg. Whisk until well blended. Add the buttermilk, sour cream, canola oil, and vanilla extract. Mix until smooth.
- Step 4: Combine the Dry Ingredients - In a separate bowl, whisk together the all-purpose flour, baking powder, and salt. Gradually add this dry mixture to the wet ingredients, stirring gently until just combined. Be careful not to overmix; a few lumps are okay.
- Step 5: Pour the Batter - Carefully pour the batter over the arranged pineapple and cherries in the cake pan, spreading it evenly with a spatula.
- Step 6: Bake the Cake - Bake in the preheated oven for 35-40 minutes, or until a toothpick inserted into the center comes out clean. Keep an eye on it to ensure it doesn’t overbake.
- Step 7: Cool and Flip - Once baked, remove the cake from the oven and let it cool in the pan for about 10 minutes. Carefully run a knife around the edges to loosen it, then place a plate over the pan and flip it upside down to release the cake. Gently lift the pan to reveal the beautiful pineapple topping.
- Step 8: Serve and Enjoy - Allow the cake to cool completely before slicing. Serve it plain or with a dollop of whipped cream for an extra indulgent treat!
Equipment
- 9-inch round cake pan
- Mixing Bowls
- Measuring cups and spoons
- Whisk
- Spatula
- Cooling Rack
Notes
- Ensure your butter is at room temperature for easier mixing with the sugar and egg.
- Use fresh pineapple for an even more vibrant flavor if desired.
- Let the cake cool before flipping to avoid any topping mishaps.
- For a more intense pineapple flavor, use pineapple juice in place of buttermilk.
