Classic Pineapple Upside-Down (Printable version)

Buttery vanilla cake topped with caramelized pineapple rings and cherries, baked until golden and inverted for serving.

# What You Need:

→ Topping

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

# Step-by-step guide:

01 - Preheat the oven to 350°F. Grease a 9-inch round cake pan.
02 - Melt 1/4 cup butter and pour it evenly on the bottom of the prepared pan. Sprinkle 3/4 cup light brown sugar over the melted butter.
03 - Place the pineapple rings over the sugar layer. Position a maraschino cherry in the center of each pineapple ring.
04 - In a mixing bowl, beat 1/2 cup softened butter and 1 cup granulated sugar together until light and fluffy.
05 - Add eggs one at a time to the butter mixture, beating well after each addition, then mix in 1 teaspoon vanilla extract.
06 - In a separate bowl, whisk 1 1/2 cups flour, 1 1/2 teaspoons baking powder, and 1/2 teaspoon salt together.
07 - Add the dry ingredients to the wet mixture in three parts, alternating with 1/2 cup whole milk, beginning and ending with flour. Stir gently until just combined.
08 - Pour the batter evenly over the pineapple and cherry layer, smoothing the surface with a spatula.
09 - Bake for 40 minutes or until a toothpick inserted into the center comes out clean.
10 - Cool the cake in the pan for 10 minutes. Run a knife around the edges, then invert onto a serving plate. Serve warm or at room temperature.

# Expert Tips:

01 -
  • One flip transforms a simple batter into a showstopper that looks almost too fancy for your kitchen.
  • The caramelized pineapple edges catch the light in a way that makes people ask for the recipe before they even taste it.
  • It's foolproof enough for a Tuesday night but impressive enough for when people come over.
02 -
  • If you flip the cake and a few pineapple rings stick to the pan, just press them back onto the top of the cake—this becomes a charming accident that no one will notice.
  • The 10-minute cooling window is sacred; too short and the cake collapses, too long and it sticks like it's been glued down.
03 -
  • An offset spatula makes smoothing the batter over those pineapple rings almost meditation-like—worth digging out of the drawer.
  • If your brown sugar is hard, soften it in a low oven for five minutes before measuring so it incorporates evenly with the butter.
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