Classic Pineapple Upside-Down Cake 
A soft, buttery vanilla cake baked over caramelized pineapple rings and maraschino cherries, then flipped upside down to reveal a beautiful golden topping. This classic dessert is easy to make and perfect for family gatherings, holidays, or a weekend treat.
Ingredients
For the Pineapple Topping:
- ½ cup unsalted butter, melted
- 1 cup packed light brown sugar
- 1 can (20 oz) pineapple slices, drained
- 10–12 maraschino cherries, drained
- 2 tablespoons pineapple juice
For the Cake:
- 1½ cups all-purpose flour
- 1½ teaspoons baking powder
- ¼ teaspoon salt
- ½ cup unsalted butter, softened
- ¾ cup granulated sugar
- 2 large eggs
- 1 teaspoon vanilla extract
- ½ cup pineapple juice
- ¼ cup whole milk
Instructions
1. Prepare the oven and pan
Preheat your oven to 350°F (175°C). Grease a 9×13-inch baking pan thoroughly with butter or nonstick spray.
2. Make the pineapple topping
Pour the melted butter evenly into the bottom of the pan. Sprinkle the brown sugar evenly over the butter.
Arrange the pineapple slices in a single layer over the brown sugar. Place a maraschino cherry in the center of each pineapple ring and add extra cherries between the rings if desired.
Drizzle the 2 tablespoons of pineapple juice over the fruit.
3. Prepare the cake batter
In a medium bowl, whisk together the flour, baking powder, and salt.
In a separate large bowl, beat the softened butter and granulated sugar until light and fluffy, about 2–3 minutes.
Add the eggs one at a time, beating well after each addition. Mix in the vanilla extract.
Add the dry ingredients gradually, alternating with the pineapple juice and milk. Mix just until combined. Do not overmix.
4. Assemble
Carefully spread the cake batter evenly over the pineapple and cherries. Smooth the top with a spatula.
5. Bake
Bake for approximately 35–45 minutes, or until the cake is golden brown and a toothpick inserted into the center comes out clean.
6. Let it rest
Remove the cake from the oven and let it cool in the pan for about 10–15 minutes. Don’t let it cool completely, because the caramelized topping can stick to the pan.
7. Flip the cake
Place a large serving platter or baking sheet over the pan. Carefully but quickly flip the pan upside down.
Let the pan sit for a minute before lifting it away. If any pineapple or cherries remain stuck, simply place them back on the cake.
Serving
Allow the cake to cool slightly before slicing. It’s delicious served warm or at room temperature, especially with a scoop of vanilla ice cream or a little whipped cream.
Tips for the Best Pineapple Upside-Down Cake
- Drain the pineapple well so the cake doesn’t become watery.
- Don’t skip the 10–15 minute resting time before flipping.
- Make sure the butter and brown sugar are spread evenly for a delicious caramelized topping.
- Avoid overmixing the batter to keep the cake soft and tender.
- Store leftovers covered at room temperature for up to 2 days, or refrigerate for longer storage.