Pineapple Upside-Down Cake from Scratch

Prep time: 15 min
Cook time: 40 min
Servings: 10
Yield: 10 servings

Description

This pineapple upside-down cake from scratch is an old-fashioned German recipe. You can use Italian prunes or pitted fresh cherries instead of pineapple.

Ingredients

1/2 cup brown sugar
1/4 cup unsalted butter, melted
3 (1/2 inch thick) slices fresh pineapple, quartered
12 frozen cranberries
2/3 cup white sugar
1/2 cup unsalted butter, softened
2 large eggs
1 1/2 teaspoons baking powder
1 teaspoon vanilla extract
1/2 teaspoon almond extract
1/2 teaspoon ground cinnamon
1/4 teaspoon salt
1 1/2 cups unbleached all-purpose flour
3/4 cup milk

Directions

1 Preheat the oven to 350 degrees F (175 degrees C). Grease a 9x2 ½-inch round cake pan.
2 Combine brown sugar and ¼ cup melted butter in a bowl; spread evenly into the prepared pan. Place 10 pineapple pieces around outer edge of pan, facing the same way, place remaining 2 pieces in the center. Place 1 cranberry between each pineapple piece.
3 Beat white sugar and ½ cup softened butter together in a bowl with an electric mixer until light and fluffy. Add eggs, one at a time, beating well and scraping sides of the bowl after each addition. Beat in baking powder, vanilla extract, almond extract, cinnamon, and salt until combined.
4 Add flour and milk to batter in 3 additions, adding ½ cup flour and ¼ cup milk at a time, mixing well after each addition, until thoroughly combined.
5 Pour batter over pineapple slices, making sure batter gets between them. Spread and smooth batter using an offset spatula.
6 Bake in the preheated oven until a toothpick inserted into the center comes out clean, 40 to 45 minutes.
7 Cool cake on a wire rack for 15 to 20 minutes. Run a knife around the edges to loosen. Place a plate over pan and quickly invert to release cake, waiting a few seconds and tapping the pan several times if it doesn't immediately separate from the pan.