Homemade Pineapple Upside Down Cake

4.94 from 96 votes

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!

Prep Time10

Cook Time35

Total Time45

Course: Dessert

Cuisine: American

Servings:

Author: Lil' Luna

Equipment

9x13 baking dish

Ingredients

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 9x13-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.

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