Homemade Pineapple Upside Down Cake

Our homemade pineapple upside down cake is a family favorite with a secret ingredient that takes this classic to a whole new level!

A Slice of Nostalgia!

Grandma has been making pineapple upside down cake for decades. It’s a family FAVORITE dessert that happens to be grandpa’s favorite!

This classic recipe has been slightly adapted over the years and now includes our favorite “secret” ingredient: almond extract. We know not everyone loves this extract (you can use vanilla extract instead), but no matter what you use the result is a simple buttery cake turned moist, gooey and upside down with caramelized pineapple slices on top. PURE HEAVEN!

Not only does it prep in minutes (10 to be exact) and has simple ingredients and steps, but it looks AMAZING (and tastes amazing)! It truly is a show-stopper that definitely turns heads at every function.

This homemade pineapple upside-down cake recipe is perfect all year long, but is an especially good summertime dessert along with our cupcake version!

Ingredients

PREP TIME: 10 minutes COOK TIME: 35 minutes

• 1 cup unsalted butter, divided – or use salted butter
• 1½ cups packed light brown sugar divided
• 1 (20-ounce) can pineapple rings in juice – Measure out ½ cup of juice and drain the excess liquid. Leave the canned pineapple pieces in a colander to finish draining or pat dry with a paper towel (fresh pineapple can be used – just peel and cut accordingly; you will still also need pineapple juice)
• 10-12 maraschino cherries
• 2 cups all-purpose flour – see How to Measure Flour
• 2 teaspoons baking powder
• 1 teaspoon salt – Reduce if using salted butter.
• ½ cup granulated sugar
• 2 large eggs- room temperature
• ½ cup milk – We use 2% but whole milk or 1% work also.
• 1 teaspoon almond extract (optional) – or teaspoon vanilla extract
• optional nuts – Sprinkle chopped walnuts or pecans in the bottom of the baking dish.

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how to make Homemade pineapple upside down cake

1. PREP. Preheat the oven to 350°F. Grease a 9×13-inch baking dish.
2. SAUCE. Melt ½ cup butter in a medium pot over medium heat. Set remaining ½ cup butter aside to soften. Stir 1 cup brown sugar into butter in the pot and bring to a boil, stirring frequently. Continue boiling for 1 minute, then pour the melted butter mixture into the prepared pan.
3. ADD FRUIT. Drain can of pineapple slices, reserving ½ cup of the juice, and place whole rings into the bottom of the cake pan. Trim the rings as needed to cover the bottom. Place a cherry in the center of each pineapple slice. Set aside.
4. BATTER. In a medium bowl, whisk 2 cups of all-purpose flour, 2 teaspoons of baking powder, and 1 teaspoon of salt. Set aside.
   • In a large bowl, beat softened ½ cup butter, ½ cup granulated sugar, and remaining ½ cup brown sugar with a hand mixer on medium speed until well combined. Add 2 eggs and blend well.
   • Add the dry ingredients to the sugar mixture and beat until well combined. While still mixing, add ½ cup milk, ½ cup of reserved pineapple juice, and 1 teaspoon of almond extract. Carefully pour the cake batter in and spread over the pineapple slices.
5. BAKE. Bake for 35–40 minutes until the middle is cooked through and a toothpick inserted in the center comes out clean. Let cool for at least 30 minutes.
6. SERVE. Use a sharp paring knife or a rubber spatula and slide it around the inner perimeter of the pan. Place the serving plate (or serving platter), larger than the cake, over the top of the cake and flip. Allow it to sit for another few minutes before carefully removing the pan and let the cake cool.
   • Serve this homemade pineapple upside down cake warm or cold with a scoop of Vanilla Ice Cream.

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4.94 from 96 votes

Homemade Pineapple Upside Down Cake

By: Lil’ Luna

Our homemade pineapple upside down cake is a family favorite with a secret ingredient that takes this classic to a whole new level!

Servings: 12

Prep: 10 minutes mins

Cook: 35 minutes mins

Total: 45 minutes mins

Cook ModePrevent your screen from going dark

Equipment

• 9×13 baking dish

Ingredients 

1x2x3x

• ▢ 1 cup unsalted butter, divided
• ▢ 1½ cups packed light brown sugar, divided
• ▢ 1 (20-ounce) can pineapple rings in juice
• ▢ 10 maraschino cherries
• ▢ 2 cups all-purpose flour
• ▢ 2 teaspoons baking powder
• ▢ 1 teaspoon salt
• ▢ ½ cup granulated sugar
• ▢ 2 eggs
• ▢ ½ cup milk
• ▢ 1 teaspoon almond extract

Instructions 

• Preheat the oven to 350°F. Grease a 9×13-inch baking dish.
• Melt ½ cup butter in a medium pot over medium heat. Set remaining ½ cup butter aside to soften.
• Stir 1 cup brown sugar into butter in the pot and bring to a boil, stirring frequently. Continue boiling for 1 minute, then pour into the prepared pan.
• Drain pineapple rings, reserving ½ cup of the juice, and place rings into the bottom of the pan. Place a cherry in the middle of each ring. Set aside.
• In a medium bowl, whisk flour, baking powder, and salt. Set aside.
• In another medium bowl, beat softened ½ cup butter, granulated sugar, and remaining ½ cup brown sugar with a hand mixer until well combined. Add eggs and blend well.
• Add flour mixture to wet mixture and beat until well combined.
• While still mixing, add milk, ½ cup reserved pineapple juice, and almond extract.
• Carefully spread batter over pineapple slices.
• Bake for 35–40 minutes, or until the middle is cooked through and a toothpick inserted in the center comes out clean. Let cool for at least 30 minutes.
• Slide a sharp paring knife or a rubber spatula around the inner perimeter of the pan. Invert a serving platter larger than the cake over the top of the pan. Place one hand on the platter and one hand on the bottom of the pan, then flip. Allow the cake to sit for another few minutes with the pan still covering it, then carefully remove the pan and enjoy!

Video

Notes

Different pans.

• Large cast iron skillet. Preheat the skillet in a 325°F oven. Add the pineapple, cherries, and batter, and bake for about 40-45 minutes.
• Bundt pan. Bake at 350°F for 35-40 minutes or until done.
• Two- 9-inch cake rounds. Bake at 375°F for 30-35 minutes or until done.

Make ahead of time.  Make 1-2 days ahead of time and store, covered, on the counter or in the fridge. You can also wrap it with plastic and foil and freeze it for up to 2 months.

Store leftover cake covered with plastic or in an airtight container at room temperature for up to 2 days, in the fridge for about 3 days, or in the freezer for about 2 months. 

Nutrition

Serving: 1slice, Calories: 373kcal, Carbohydrates: 54g, Protein: 4g, Fat: 17g, Saturated Fat: 10g, Polyunsaturated Fat: 1g, Monounsaturated Fat: 4g, Trans Fat: 1g, Cholesterol: 69mg, Sodium: 219mg, Potassium: 158mg, Fiber: 1g, Sugar: 37g, Vitamin A: 531IU, Vitamin C: 0.01mg, Calcium: 78mg, Iron: 1mg

Nutrition information is automatically calculated, so should only be used as an approximation.

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