Pineapple Upside-Down Cake (Printer-friendly)

Buttery vanilla cake with caramelized pineapple rings and cherries, baked to golden perfection.

# What You 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. Thoroughly grease a 9-inch round cake pan with butter or cooking spray.
02 - Melt 1/4 cup butter and pour evenly into the prepared pan. Sprinkle brown sugar across the butter in a uniform layer.
03 - Place pineapple rings over the brown sugar mixture. Position one maraschino cherry in the center of each pineapple ring for classic presentation.
04 - In a large mixing bowl, beat 1/2 cup softened butter and granulated sugar together until pale and fluffy, approximately 3-4 minutes.
05 - Add eggs one at a time, mixing thoroughly after each addition. Blend in vanilla extract until fully incorporated.
06 - In a separate bowl, whisk together flour, baking powder, and salt until evenly combined.
07 - Add flour mixture to the butter mixture in three portions, alternating with milk in two portions. Begin and end with flour. Mix until just combined, taking care not to overmix.
08 - Spread batter evenly over the pineapple arrangement, smoothing the top with a spatula. Bake for 38-42 minutes until a toothpick inserted into the center emerges clean.
09 - Allow cake to rest in the pan for 10 minutes. Run a knife around the edges to release, then carefully invert onto a serving plate. Serve warm or at room temperature.

# Cooking Tips:

01 -
  • The combination of caramelized brown sugar and juicy pineapple creates those nostalgic flavors everyone remembers from childhood but better than you remember
  • This stunning dessert looks like it took hours to make but comes together with simple ingredients you probably already have in your pantry
02 -
  • Don't wait longer than 10 minutes to invert the cake or the caramel will harden and stick to the pan instead of releasing onto your cake
  • Adding a tablespoon of pineapple juice to the batter intensifies the pineapple flavor throughout the entire cake
03 -
  • Use a light-colored cake pan rather than dark metal, which can cause the edges to overcook and the caramel to burn before the center is done
  • If your fruit has shifted during baking, quickly and gently rearrange it with a fork during that 10-minute cooling window before inverting
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