A classic homemade pineapple upside down cake made with a moist vanilla buttermilk cake base topped with caramelized pineapple rings dotted with maraschino cherries.

Pineapple upside down cake on white plate.

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Pineapple Upside Down Cake with Buttermilk

I’ve never met a pineapple dessert that I didn’t like whether it’s a light and fluffy pineapple fluff dessert or this retro homemade upside down cake!

This recipe for pineapple upside down cake is an American classic just like angel food cake! The soft vanilla cake base has moist texture from buttermilk and the caramelized pineapple slices dotted with maraschino cherries on top are sweet and juicy.

Ingredient Notes

Pineapple upside down cake ingredients on counter.

Find the full printable recipe with specific measurements below.

  • Pineapple: I use canned pineapple slices because it’s what Grandma used! Drain the pineapple juice and blot the slices dry before adding them to your pan.
  • Maraschino cherries: These are sweet cherries that are preserved in syrup. Their bright red color pops in this cake!
  • For the cake: This is a classic vanilla buttermilk cake that uses flour, baking powder, granulated white sugar, light brown sugar, butter and buttermilk.
  • Vanilla extract: Vanilla extract balances the sweet, rich taste of this cake.

How to Make Pineapple Upside Down Cake

Showing how to make pineapple upside down cake in a 6 step collage.
  • Prepare the cake pan. Spray your pan with non-stick cooking spray and line the bottom with parchment paper to ensure that the topping doesn’t stick to the bottom.
  • Prepare topping. Pour the melted butter into the bottom of the pan then sprinkle over the brown sugar. Place the pineapple rings attractively into the pan, also placing 6 pineapple halves upright around the sides of the pan. Put a cherry into the middle of each pineapple ring. 
  • Combine dry ingredients. Stir the flour, baking powder, and salt together in a small bowl.
  • Combine wet ingredients. Whisk butter and sugars together in a large bowl then add the eggs and vanilla. Continue to whisk until smooth.
  • Make buttermilk cake batter. Add 1/3 flour mixture to the wet ingredients, then half of the buttermilk. Repeat the steps until everything has been added. Continue to whisk after each addition. Pour the batter over the pineapple and spread it so it’s even.
  • Bake. The cake will bake for 45 – 50 minutes. Use foil to tent the cake halfway through the baking time so it doesn’t over-brown. Let the cake rest for at least 10 minutes before placing a serving platter over the top of the cake and carefully flipping it upside down. Remove the parchment and let cool completely before serving.

Tips and Variations

  • Blot the pineapple rings of excess juice before placing them into the bottom of the pan. This helps prevent the cake from being too soggy on top.
  • Make your own homemade buttermilk or use my vanilla cake mix.
  • Arrange the pineapples carefully into the bottom of the pan. Remember that what you see at the bottom of the pan is what will be the top of your cake.
  • Let the classic pineapple upside-down cake sit for 10 minutes before releasing it from the pan. If you try to release it too soon, it may fall apart.
  • Serve the cake warm with a dollop of whipped cream and extra cherry on top.
Pineapple upside down cake on white platter.

Storing

  • Refrigerator: Store any leftover cake in the refrigerator in an airtight container. You can keep it this way for up to 3 days. 
  • Freezing: The best way to freeze leftovers is to cut it into individual slices and wrap them tightly in plastic wrap. Wrapping them again in aluminum foil is a great way to prevent freezer burn. Keep slices frozen for up to 3 months. Thaw overnight in the refrigerator.
Slice of Pineapple upside down cake on a white plate.

More must-try classic dessert recipes include blueberry buttermilk cake and buttermilk pie!

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Pineapple upside down cake on white platter.

Pineapple Upside Down Cake Recipe

5 from 8 votes
Recipe by: Jamielyn Nye
Prep Time: 20 minutes
Cook Time: 45 minutes
Cool Time: 45 minutes
Total Time: 1 hour 50 minutes
Servings: 8
A classic homemade pineapple upside down cake made with a moist vanilla buttermilk cake base topped with caramelized pineapple rings dotted with maraschino cherries.
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Ingredients 

Topping

  • 10 pineapple slices , patted dry with a paper towel
  • 7 maraschino cherries , patted dry with a paper towel
  • 4 Tablespoons unsalted butter , melted
  • ⅓ cup light brown sugar

Cake

  • 1 ½ cups all-purpose flour
  • 1 ½ teaspoons baking powder
  • ¼ teaspoon salt
  • 6 Tablespoons unsalted butter , melted
  • ¾ cup granulated sugar
  • ¼ cup light brown sugar
  • 2 large eggs , at room temperature
  • 1 ½ teaspoons vanilla extract
  • ⅔ cup buttermilk

Instructions

  • Preheat the oven to 350°F. Spray a 9-inch cake pan that is at least 2 inches deep (or a deep pie dish) with nonstick cooking spray. Line the bottom with parchment paper to avoid the cake sticking.

Topping

  • Cut 3 pineapple slices in half. In the bottom of the cake pan, pour the 4 Tablespoons melted butter, tilting to coat the bottom. Sprinkle evenly with the 1/3 cup brown sugar. Arrange the blotted whole pineapple slices over the brown sugar and place the blotted pineapple halves upright evenly around the sides of the pan. Add 1 cherry to the center of each pineapple slice.

Cake

  • In a small bowl, stir the 1 1/2 cups flour, 1 1/2 teaspoons baking powder, and 1/4 teaspoons salt until combined.
  • In a large bowl, whisk together the 6 Tablespoons butter, 3/4 cup granulated sugar, and 1/4 cup brown sugar until well combined. Whisk in 2 large eggs and 1 1/2 teaspoons vanilla until smooth.
  • Mix in 1/3 of the flour mixture, followed by 1/3 cup of the buttermilk. Repeat with remaining remaining flour mixture and buttermilk, mixing well after each addition. Pour the batter evenly over the top of the pineapples. It's ok if some of the pineapples on the edge are still visible.
  • Bake 45 to 50 minutes, or until golden brown and a toothpick inserted in the center comes out clean. Tent the cake with foil halfway through bake time to prevent the top from getting too brown before the center has a chance to fully cook. Some cake may stick to the foil, but don't worry it won't show.
  • Let cool at least 10 minutes in the pan. Run a knife around the edges of the cake to loosen it from the pan. Place a serving platter over the top of the cake and carefully flip it upside down. Remove the parchment and let cool completely.

Last step: Please leave a comment and rating after you make the recipe.

Notes

Storage: Store in an airtight container up to 3 days.
Freeze: Wrap individual slices in plastic wrap and freeze up to 3 months. Thaw at room temperature, unwrapped, before serving.

Nutrition

Calories: 557kcal, Carbohydrates: 85g, Protein: 9g, Fat: 21g, Saturated Fat: 9g, Polyunsaturated Fat: 3g, Monounsaturated Fat: 8g, Trans Fat: 0.5g, Cholesterol: 79mg, Sodium: 120mg, Potassium: 292mg, Fiber: 2g, Sugar: 49g, Vitamin A: 493IU, Vitamin C: 7mg, Calcium: 102mg, Iron: 1mg

Nutrition provided is an estimate. It will vary based on specific ingredients used.