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A pineapple upside down cake on top of a white pedestal plate.
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Homemade Pineapple Upside Down Cake

This recipe for homemade Pineapple Upside Down Cake is a must try! A soft, moist, white crumb cake with pineapple juice is baked inside a cake pan with pineapple ring slices, maraschino cherries, and topped with a sweet brown sugar caramelized glaze.
Course Dessert
Cuisine American
Keyword homemade pineapple upside down cake recipe, pineapple upside down cake
Prep Time 25 minutes
Cook Time 40 minutes
Total Time 1 hour 5 minutes
Servings 10
Calories 408kcal
Author Jessica - Together as Family

Equipment

Ingredients

Pineapple Cherry Brown Sugar Topping

  • 3/4 cup packed light brown sugar
  • 4 tablespoons butter
  • 2 tablespoons pineapple juice (from the canned pineapple)
  • 1 can (20 oz) pineapple rings
  • 12 maraschino cherries without stems

Pineapple Vanilla Cake

  • 2 cups all-purpose flour
  • 3/4 cup granulated sugar
  • teaspoons baking powder
  • ½ teaspoon table salt
  • ¼ teaspoon baking soda
  • 2 large eggs
  • 3/4 cup buttermilk
  • 1/4 cup pineapple juice (from the canned pineapple)
  • 8 tablespoons (1 stick) butter melted & cooled slightly
  • 1 teaspoon vanilla extract

Instructions

  • Preheat oven to 350° F.
    Prepare a 9-inch OR 10-inch round cake pan, with higher sides on it (2 inches), and spray with cooking spray. Set aside.

Pineapple Cherry Brown Sugar Topping

  • In a small saucepan, over medium heat, combine the brown sugar, butter, and pineapple juice. Using a silicone whisk, heat and stir occasionally, until the butter is melted and the sugar is dissolved.
    Once melted and smooth, pour it into the prepared round cake pan.
    * This will only take a few minutes. No need to let it boil or anything. Just until melted.
  • Place 1 pineapple ring in the center of the cake pan on top of the brown sugar mixture. Take 5 pineapple rings and cut them in half so you're left with 2 half moon shapes from each pineapple ring. Arrange the halved rings on the outside of the middle one, laying them all in the same direction.
    Place a maraschino cherry into the center of each pineapple ring. You will use one for the center ring and one in each of the half moon shaped pineapple rings on the outside.
    How to make this cake recipe with step be step instructions with pictures.

Pineapple Vanilla Cake

  • In a large mixing bowl, whisk together the flour, sugar, baking powder, salt, and baking soda. Make a well in the center and set aside.
  • In a small mixing bowl, or use a glass measuring cup, add the eggs and whisk. Add the buttermilk, pineapple juice, melted butter, and vanilla extract. Whisk until combined well. Pour into the well of the dry ingredients.
    How to make this cake recipe with step be step instructions with pictures.
  • Gently stir together with a wooden mixing spoon, or rubber spatula, just until combined and no flour streaks remain in the batter.
  • Scoop dollops of the cake batter on top of the pineapple rings inside the cake pan. Gently spread it out making sure to avoid messing up the pineapple layer and the brown sugar mixture.
  • Place the cake pan onto a foil-lined cookie sheet just in case anything spills over. it's important to use a cake pan with at least 2-inch high sides on it to avoid spillage while baking.
    How to make this cake recipe with step be step instructions with pictures.
  • Cook for 35-45 minutes or until a toothpick inserted into the center comes out clean.
    * Loosely tent the cake pan with tin foil if it's over-browning towards the end of the cook time.
  • Allow the cake to cool in the pan for 20 minutes before inverting it onto a serving platter.
    Cool to room temperature, or serve slightly warmed, and slice it like you would a pie! We love this served with whipped cream and an extra cherry on top.
    How to make this cake recipe with step be step instructions with pictures.

Notes

Cake Pan : This recipe has been made and tested with a 9-inch round cake pan. Do not use smaller than that. As it cooks, the cake does rise quite a bit so if you use something smaller, the cake batter will spill over. You can also use a 10-inch round cake pan if that's what you have. I would also think that this recipe would work in a 9x13 baking pan. You might need more pineapple rings if using the rectangle shape 9x13 pan. 
Cookie Sheet for Baking : In the directions above it mentions putting the cake pan on top of a tin foiled lined cookie sheet. This is optional, and it's just incase the cake batter spills over. But if you are using the correct size pan, then this should not happen, I just like to use it just in case. 
The products linked above are affiliate links, meaning that if you purchase from that link I earn a very small percentage. As always, I only share products that I actually have in my own kitchen. 
 

Nutrition

Calories: 408kcal | Carbohydrates: 64g | Protein: 5g | Fat: 16g | Saturated Fat: 9g | Polyunsaturated Fat: 1g | Monounsaturated Fat: 4g | Trans Fat: 1g | Cholesterol: 75mg | Sodium: 292mg | Potassium: 276mg | Fiber: 2g | Sugar: 43g | Vitamin A: 535IU | Vitamin C: 6mg | Calcium: 105mg | Iron: 2mg