Homemade Pineapple Upside Down Cake

5 from 4 votes

This pineapple upside down cake features a soft vanilla cake with the perfect pineapple and cherry glazed top.

Prep Time10

Cook Time45

Total Time55

Course: Dessert

Cuisine: American

Keyword: Pineapple Upside Down Cake Recipe

Servings:

Calories: 414kcal

Preheat the oven to 350°F. Line a 10-inch round cake pan with parchment paper.
Combine the ingredients for the pineapple glaze (butter, brown sugar, cinnamon) in a saucepan and melt them together for 5 minutes until the sugar dissolves, and pour the melted butter mixture into the prepared pan.
Arrange the pineapple slices in a single layer over the sugar mixture, and place a maraschino cherry in the center of each pineapple slice. Set this aside for later.
Cream butter, sugar, and cream cheese in a stand mixer until light and fluffy.
With mixer on low speed beat in the eggs one at a time, followed by the vanilla and crushed pineapple until combined.
In a medium bowl, combine dry ingredients.
Slowly add dry ingredients until combined. Do not over mix!
Carefully pour batter over the pineapple and cherry glaze that is already in the pan. Bake for 30 to 40 minutes. Let cool for 5 minutes.
Invert onto a serving platter. The pineapples and cherry glaze will become the top, and your cake will be on the bottom.

You can buy pre-cut parchment paper rounds to make lining the pan even easier.
You could also bake your cake in a cast iron skillet or a bundt cake pan.
Don’t over-mix the batter, or your cake will be tough and rubbery.
Oven temperatures vary and may need to be recalibrated periodically to ensure they are accurate. Make sure to check your cake at the lower end of the recommended baking time.