Name: Classic Pineapple Upside-Down Cake with Maraschino Cherries
Prep time: 15 min
Cook time: 45 min
Total time: 1 h 10 min
Yield: 9 slices
Cuisine: American
Ingredients: 4 tbsp unsalted butter (melted); 2/3 cup packed light brown sugar; 1 can pineapple rings in juice (20 oz, drained, juice reserved); 9 maraschino cherries (drained and patted dry); 1 1/2 cups all-purpose flour; 1 1/2 tsp baking powder; 1/4 tsp salt; 1/2 cup unsalted butter (softened to room temperature); 3/4 cup granulated sugar; 2 large eggs (room temperature); 1 tsp vanilla extract; 1/2 cup reserved pineapple juice (from the can)

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This recipe has been in my family's rotation for as long as I can remember. There is something about the moment you flip that pan and see those golden pineapple rings and bright cherries staring back at you that never gets old.

We are making the kind of cake that looks like it took serious effort but comes together with pantry staples and about 15 minutes of real work. You'll find it's one of those recipes that builds confidence in the kitchen, one beautiful flip at a time.

Classic Pineapple Upside-Down Cake with Maraschino Cherries

A buttery, caramelized classic that flips into something truly showstopping every single time.

4.9 (202 reviews)

Prep15 min

Cook45 min

Cooling before flip10 min

Total1 hr 10 min

Serves9 slices

Ingredients

Caramel Pineapple Topping

4 tbsp unsalted butter , melted
2/3 cup packed light brown sugar
1 can pineapple rings in juice , 20 oz, drained, juice reserved
9 maraschino cherries , drained and patted dry

Cake Batter

1 1/2 cups all-purpose flour
1 1/2 tsp baking powder
1/4 tsp salt
1/2 cup unsalted butter , softened to room temperature
3/4 cup granulated sugar
2 large eggs , room temperature
1 tsp vanilla extract
1/2 cup reserved pineapple juice , from the can

Instructions

Preheat your oven to 350 degrees F. Place a 9-inch round cake pan or a 9x9 square pan on your counter and have it ready to go.

Pour the 4 tablespoons of melted butter directly into the pan and tilt it gently so the butter coats the bottom evenly.

Sprinkle the brown sugar over the melted butter in an even layer. Press it down lightly with your fingers so it sits flat.

Arrange the drained pineapple rings on top of the brown sugar. You'll fit one ring in the center and about 7 to 8 rings around it depending on your pan. Press a maraschino cherry into the center of each ring and tuck one into any gaps between rings.

In a medium bowl, whisk together the flour, baking powder, and salt. Set this aside.

In a large bowl, beat the softened butter and granulated sugar together with a hand mixer or a sturdy wooden spoon until the mixture looks pale and slightly fluffy, about 2 to 3 minutes.

Add the eggs one at a time, mixing well after each one. Stir in the vanilla extract.

Add half the flour mixture to the butter mixture and stir gently until just combined. Pour in the pineapple juice and stir again. Add the remaining flour mixture and stir until no dry streaks remain. Do not overmix.

Carefully spoon the batter over the arranged pineapple rings and spread it into an even layer with the back of a spoon or a spatula. The batter is thick, so take your time and be gentle so you don't shift the fruit.

Bake for 40 to 45 minutes, until the top of the cake is golden brown and a toothpick inserted into the center comes out clean.

Remove the pan from the oven and let it cool on a wire rack for exactly 10 minutes. This rest time is important. Too soon and the topping slides, too long and the caramel sticks.

Run a butter knife around the edge of the pan to loosen the cake. Place a large plate or cutting board over the top of the pan, hold both firmly together, and flip in one confident motion. Lift the pan off slowly and let the cake settle. Rearrange any cherries that shifted and serve warm.

Tips & Notes

Pat your maraschino cherries very dry with paper towels before placing them. Extra moisture can cause them to sink or make the topping watery.
Room temperature butter and eggs make a real difference in this batter. Pull them out about 30 minutes before you start.
If your pan is older or tends to stick, lay a circle of parchment paper over the butter before adding the brown sugar for extra insurance.
Do not skip the 10-minute rest before flipping. Set a timer so you don't forget. That window is the sweet spot for a clean release.
Canned pineapple in juice works better here than pineapple in syrup. The juice is less sweet and gives the cake a fresher pineapple flavor.
Leftovers reheat beautifully. A quick 20-second burst in the microwave brings the caramel back to life.

Storage: Store leftover cake covered at room temperature for up to 2 days, or refrigerate for up to 4 days. Bring slices to room temperature or warm briefly before serving for the best texture and flavor.

Nutrition per serving · estimated

380 Cal

16g Fat

57g Carbs

4g Protein

1g Fiber

38g Sugar

160mg Sodium

Classic Pineapple Upside-Down Cake with Maraschino Cherries step-by-step

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Why the Flip Works Every Time

The caramel layer is what makes this cake so forgiving and so reliable. Brown sugar and butter melt together in the bottom of the pan during baking and create a sticky, glossy coating that bonds to the pineapple and releases cleanly when you flip.

The 10-minute rest is doing real work here. The caramel needs that brief cooling period to firm up just enough so everything holds together without seizing onto the pan. Trust the process and the flip will reward you every time.

Making It Your Own

This recipe is a great base for small variations once you feel comfortable with it. Swap the pineapple rings for fresh mango slices or peach halves and the same technique applies perfectly.

You can also add a pinch of cinnamon or a splash of coconut extract to the batter for a slightly tropical twist. The core method stays exactly the same, and that's what makes it such a confidence-building recipe to have in your regular rotation.