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Pineapple Upside-Down Cake That’s Old-School Perfection

You know that moment when you take your first forkful of a warm, sticky-sweet pineapple upside-down cake and suddenly you’re right back at your grandma’s kitchen table? That’s exactly the feeling this recipe brings me every single time. The caramelized edges, the buttery cake, and that glorious pineapple slice topped with a maraschino cherry — it’s like a bite of nostalgia wrapped in golden brown goodness. If you’re craving a dessert that feels like a big, cozy hug from the past, this old-school pineapple upside-down cake is where it’s at. Plus, it’s easier than you’d think, even if you haven’t baked since, well, forever!

Quick Facts

Yield: Serves 8
Prep Time: 15 minutes
Cook Time: 40 minutes
Total Time: 55 minutes

Ingredients

For the Main Dish:

1/4 cup unsalted butter (half a stick)
2/3 cup packed light brown sugar
1 (20 oz) can sliced pineapple in juice, drained (reserve juice)
8–10 maraschino cherries
1 1/2 cups all-purpose flour
2 tsp baking powder
1/4 tsp salt
1/2 cup granulated sugar
1/4 cup pineapple juice (reserved from the can, plus extra as needed)
1/3 cup vegetable oil
1 large egg
1 tsp vanilla extract

How I Make It

Step 1:

Preheat your oven to 350°F. Melt 1/4 cup butter in a 9-inch cake pan right on the stove or in the oven (watch carefully so it doesn’t brown). Sprinkle the 2/3 cup light brown sugar evenly over the melted butter—this is the sweet caramel base that’ll give your cake that signature golden top.

Step 2:

Arrange the sliced pineapple in a single layer over the sugar, placing a maraschino cherry in the center of each ring. This step is what takes this cake from good to wow—give it some love and space so each slice shines through after flipping.

Step 3:

In a separate bowl, whisk together flour, baking powder, and salt. In another bowl, mix sugar, pineapple juice, vegetable oil, egg, and vanilla until smooth. Slowly stir the dry ingredients into the wet until just combined—don’t overmix or the cake will be dense.

Step 4:

Carefully pour the batter over the pineapple and cherries in the pan, smoothing the top as best you can without disturbing the fruit arrangement.

Step 5:

Bake for about 40 minutes, until a toothpick inserted in the center comes out clean and the edges look set and golden.

Step 6:

Let the cake cool in the pan on a wire rack for about 10 minutes (this is key to preventing the caramel from sticking too much). Run a knife around the edges to loosen, then place a serving plate on top and quickly—carefully!—flip it over to reveal that glossy, caramelized fruit masterpiece.

Variations & Tips

Swap pineapple rings for peach slices or apple slices for a seasonal twist.
Use dark brown sugar for a richer, molasses-y caramel flavor.
Lightly brush pineapple rings with melted butter to make them extra juicy and caramelized.
If your cake sticks, warm the bottom pan slightly or add a bit more butter next time.
Add a teaspoon of ground cinnamon to the batter for a warm spice note.
Use fresh pineapple if you prefer, but reduce the juice slightly to keep the batter consistency right.

How I Like to Serve It

I love serving this cake warm, right out of the pan, with a scoop of vanilla ice cream or a dollop of whipped cream. It’s perfect for summer barbecues or those cozy fall afternoons when you want a simple dessert that’s a little nostalgic. It’s also a total showstopper on holidays, like Easter brunch or a casual Christmas dessert table.

Notes

Store leftovers covered at room temperature for up to 2 days (though it’s best eaten fresh!).
Reheat slices gently in a microwave for 15-20 seconds if you want to bring back that warm, gooey texture.

Closing: This pineapple upside-down cake always brings a perfect slice of old-school sweetness that’s simply impossible to resist.