Pineapple Upside-Down Cake from Scratch

This is an old-fashioned upside-down cake recipe from my German grandmother from scratch. She used this same cake batter for many different fruits as an alternative to pineapple. She often used fresh Italian prunes or pitted fresh cherries. My grandparents owned a bakery and this cake was very popular in the 1950s and 1960s. Serve warm or at room temperature with whipped cream.

• Preparation Time: 15 mins
• Cooking Time: 40 mins
• Total Time: 55 mins
• Calories: 319 Calories

Ingredients

• 1 teaspoon vanilla extract
• ¼ teaspoon salt
• ½ teaspoon ground cinnamon
• ¾ cup milk
• ½ teaspoon almond extract
• 1 ½ teaspoons baking powder
• ⅔ cup white sugar
• 2 large eggs
• ½ cup unsalted butter, softened
• ½ cup brown sugar
• ¼ cup unsalted butter, melted
• 1 ½ cups unbleached all-purpose flour
• 3 (1/2 inch thick) slices fresh pineapple, quartered
• 12 frozen cranberries

Recipe Instructions

Step 1

Bake in the preheated oven until a toothpick inserted into the center comes out clean, 40 to 45 minutes.

Step 2

Preheat the oven to 350 degrees F (175 degrees C). Grease a 9-inch diameter, 2 1/2-inch tall round cake pan.

Step 3

Stir brown sugar and melted butter together in a bowl. Spread evenly over the bottom of the prepared cake pan. Place pieces of pineapple on top of brown sugar mixture and around the outer edge of the pan, all facing the same way. Place 2 pieces in the center. Place a cranberry between each pineapple piece.

Step 4

Beat white sugar and softened butter together using an electric mixer in a bowl until light and fluffy. Add eggs, one at a time, beating well and scraping the sides of the bowl after each addition. Pour in baking powder, vanilla extract, almond extract, cinnamon, and salt. Mix well.

Step 5

Add 1/2 cup flour and 1/4 cup milk to batter at a time, mixing well after each batch until thoroughly blended.

Step 6

Pour batter over pineapple slices, making sure batter gets between them. Spread and smooth batter using an offset spatula.

Step 7

Remove cake from the oven and let cool on a wire rack for 15 to 20 minutes. Run a knife around the edges of the cake to loosen. Place a plate over the cake pan and quickly invert, waiting a few seconds for it to fall if it doesn't immediately separate from the pan.