Pineapple Upside-Down Cake (Printable)

Buttery vanilla cake with caramelized pineapple rings and cherries, baked golden and served inverted.

# 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 tsp vanilla extract
09 - 1 1/2 cups all-purpose flour
10 - 1 1/2 tsp baking powder
11 - 1/2 tsp salt
12 - 1/2 cup whole milk

# Preparation Steps:

01 - Preheat oven to 350°F. Generously grease a 9-inch round cake pan with butter or cooking spray.
02 - Melt 1/4 cup butter and pour into the bottom of the prepared pan. Sprinkle brown sugar evenly over the melted butter, creating an even layer.
03 - Place pineapple rings over the sugar-butter mixture, spacing them evenly. Nestle a maraschino cherry in the center of each pineapple ring.
04 - In a large mixing bowl, beat softened butter and granulated sugar together until light, fluffy, and pale yellow, about 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 flour mixture to the butter mixture in three additions, alternating with milk and beginning and ending with flour. Mix until just combined—do not overmix.
08 - Spoon batter over the pineapple arrangement, spreading gently to create an even layer. Bake for 38-42 minutes until golden and a toothpick inserted into the center emerges clean.
09 - Let cake cool in the pan for 10 minutes. Run a thin knife around the edges to loosen, then carefully invert onto a serving plate. Serve warm or at room temperature.

# Expert Suggestions:

01 -
  • That moment when you flip the pan and the pineapple glistening with caramel reveals itself like a hidden treasure
  • The way the house fills with the most incredible buttery vanilla scent while it bakes
  • How it looks impressive but comes together with ingredients you probably already have
02 -
  • Let the cake cool exactly 10 minutes before flipping—too soon and it falls apart, too late and the caramel sticks
  • The pan will be hot when you invert it, so use oven mitts and work over a cutting board to catch any drips
03 -
  • Adding 1–2 tbsp of pineapple juice to the batter intensifies the fruit flavor throughout the cake
  • Don't overmix the batter once you add the flour—just a few gentle turns until combined makes the tenderest crumb
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