Pineapple Upside Down Cake

4.25 from 4 votes

Easy pineapple upside down cake made with canned pineapple and a simple homemade cake. It's much easier than you might think!

Prep Time30

Cook Time50

Course: Cakes, Dessert

Cuisine: American

Keyword: cake, pineapple

Servings:

Calories: 431kcal

Author: Melissa Griffiths

Ingredients

For the topping:

1 can pineapple slices 20 ounces, reserve ⅓ cup of juice for cake
19 maraschino cherries stems removed
¼ cup unsalted butter melted
⅔ cup packed light brown sugar

For the cake:

1 ⅔ cups all purpose flour
1 ½ teaspoons baking powder
½ teaspoon salt
¼ cup unsalted butter melted
¼ cup canola oil
1 cup granulated white sugar
2 egg large, at room temperature
2 teaspoons vanilla extract
⅓ cup whole milk at room temperature
⅓ cup pineapple juice reserved from pineapple rings

Instructions

Preheat your oven to 350 degrees F. Line the bottom of a 9-inch round cake pan with a parchment paper round that fits the bottom and then spray the sides with cooking spray. Set aside.
Drain pineapple and reserve ⅓ cup of the juice to use in the cake (I save the remaining juice to throw in a smoothie or drink). Place pineapple slices and cherries on a plate and blot with a paper towel to remove excess moisture. Cut 3 pineapple slices in half.
Pour the melted butter into the bottom of the cake pan, and brush or swirl it to coat the entire bottom. Sprinkle the brown sugar over the top of the butter. Place the whole pineapple slices on top of the brown sugar (8 on the bottom of the pan, and with the remaining cut pineapple slices, place each pineapple half slice around the sides standing upright alternating between the slices on the bottom. Place a cherry in the center of each pineapple slice and in between the pineapple slices and around the sides.
To make the cake, in a medium mixing bowl add the butter, oil, and sugar and cream together until the mixture is light and fluffy. You can use a stand mixer or a hand mixer or just some vigorous stirring with a wooden spoon for this.
Add the eggs and vanilla, stir to combine.
In a separate medium mixing bowl add the flour, baking powder, and salt and whisk to combine.
In another small bowl mix the reserved pineapple juice and milk together.
Add the flour mixture to the creamed butter mixture alternately with buttermilk, mixing well after each addition. Pour the batter over the top of the pineapple topping. Some of the pineapple slices may still peak above the top of the cake batter, that's ok.
Bake in the center of your preheated oven for 50-60 minutes or until toothpick inserted in center of cake comes out clean (don’t go all the way down or you will just get the brown sugar bottom) . Top of the cake will be a deep golden brown and spring back when lightly touched.
Remove from the oven and allow to cool for 5 minutes in the pan. Use a knife and loosen around the edge of the cake pan, and invert out onto a serving platter. Store leftovers in an airtight container for up to 3 days in the fridge.

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