A Family Favorite: Pineapple Upside Down Cake

Some desserts come and go, trending for a moment before disappearing into recipe boxes. But a Pineapple Upside Down Cake? That’s a classic that never loses its magic. For my family, this cake has been a constant—a sweet, sticky slice of nostalgia that brings everyone to the kitchen the moment they smell it baking.

This recipe comes straight from my grandmother’s kitchen, a place where simple ingredients turned into unforgettable memories. I can still picture her flipping the warm cake onto a plate with confidence, revealing those caramelized pineapple rings like a little culinary ta-da. It felt like a trick only grandmothers could pull off.

The cake pan I use now—a perfectly sized 10" x 10" x 2.25" pineapple upside down cake pan—was passed down to me from my mother-in-law. And with every bake, it feels like I’m carrying a bit of both women’s traditions forward. That’s one of the things I love most about cooking: the way recipes become heirlooms.

And the best part? This dessert is so easy. REALLY easy. The kind of recipe you can make on a weekday, bring to a potluck, or whip up for company without breaking a sweat. And yet, it always looks beautiful and tastes like you spent all afternoon on it. My whole family loves it, and I think yours will too.

Pineapple Upside Down Cake

Ingredients

• 1 (20 oz.) can Dole Pineapple Slices (reserve juice for the cake mix)

• ¼ cup packed brown sugar

• 2 tablespoons melted butter

• 8 maraschino cherries

• 1 box yellow cake mix or pineapple cake mix

Directions

1. Preheat your oven to 350°F.

2. Melt the butter and pour it into the bottom of a pineapple upside down cake pan (10” x 10” x 2.25”).

3. Sprinkle the brown sugar evenly over the melted butter.

4. Arrange the pineapple rings on top and place a maraschino cherry in the center of each ring.

5. Prepare your cake mix according to the box instructions, substituting pineapple juice for the water. If your can doesn’t provide a full cup of juice, simply add enough water to reach 1 cup.

6. Pour the batter over the fruit and sugar mixture.

7. Bake for 40–45 minutes, or until a toothpick inserted in the center comes out clean.

8. Let the cake cool for 5 minutes, then carefully flip it onto a serving plate.

9. Admire your masterpiece—and enjoy!

There’s something so satisfying about the moment this cake leaves the pan: the glossy fruit, the caramelized edges, the buttery brown-sugar glaze dripping just a little down the sides. It’s a small celebration every single time.

If you give this classic a try, I hope it brings your home the same joy, sweetness, and togetherness it has brought mine for generations.