Pineapple Upside-Down Cake (Printable)

Buttery vanilla cake with caramelized pineapple and cherries, baked golden and served inverted for impressive presentation.

# What You'll Need:

→ Topping

01 - 1/4 cup unsalted butter
02 - 3/4 cup light brown sugar, packed
03 - 8-10 canned pineapple rings, drained
04 - 8-10 maraschino cherries

→ Cake Batter

05 - 1/2 cup unsalted butter, softened
06 - 1 cup granulated sugar
07 - 2 large eggs
08 - 1 teaspoon vanilla extract
09 - 1 1/2 cups all-purpose flour
10 - 1 1/2 teaspoons baking powder
11 - 1/2 teaspoon salt
12 - 1/2 cup whole milk

# How to Make It:

01 - Preheat oven to 350°F. Grease a 9-inch round cake pan thoroughly with butter or cooking spray.
02 - Melt 1/4 cup butter and pour into the bottom of the prepared pan. Sprinkle 3/4 cup brown sugar evenly over the melted butter.
03 - Place pineapple rings over the sugar-butter mixture. Add a maraschino cherry in the center of each pineapple ring.
04 - In a large mixing bowl, beat 1/2 cup softened butter and 1 cup granulated sugar with an electric mixer until light and fluffy, approximately 3-4 minutes.
05 - Beat in eggs one at a time, fully incorporating each before adding the next. Stir in vanilla extract.
06 - In a separate bowl, whisk together flour, baking powder, and salt until well blended.
07 - Add dry ingredients to butter mixture in three additions, alternating with milk. Begin and end with flour. Mix until just combined, being careful not to overmix.
08 - Spread batter evenly over pineapple arrangement. Smooth top with a spatula to create an even layer.
09 - Bake for 38-42 minutes until golden brown and a toothpick inserted into the center comes out clean.
10 - Cool in pan for 10 minutes. Run a knife around edges to loosen, then carefully invert onto a serving plate. Serve warm or at room temperature.

# Expert Suggestions:

01 -
  • The caramel topping seeps into the cake creating pockets of buttery sweetness in every single bite
  • It looks like you spent hours on a fancy dessert but comes together with basic pantry staples
  • The dramatic flip moment makes everyone gasp, and that kind of kitchen magic is worth keeping around
02 -
  • Wait the full 10 minutes before flipping, or the caramel will not have set and your pineapple pattern will slide right off the cake
  • Do not let the cake cool completely in the pan or the caramel will harden and stick to the bottom, ruining that beautiful presentation
  • Arranging the pineapple takes a few extra minutes but makes such a difference in how the final cake looks
03 -
  • Use a light-colored cake pan rather than dark metal to prevent the edges from overbaking before the center is done
  • Place your cake pan on a baking sheet to catch any potential caramel drips in the oven
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