Desserts / Cakes & cheesecakes
Pineapple Upside-Down Cake in a Skillet
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Rest it three minutes, then flip it onto a plate with everyone watching. One year we waited too long, and the caramel kept half the pineapple for itself. We ate it with spoons and called it pudding.
The short version
Melt butter and brown sugar in a 9-inch skillet, arrange pineapple rings and cherries on top, spread a buttermilk batter over them, and bake at 350°F for 35 to 40 minutes. Rest 3 minutes, then flip onto a plate.
What makes ours better
why ours wins the argument at dinner
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Pat the pineapple dry. Pineapple is wet. Blotting the rings on paper towels keeps the caramel thick and the cake from getting soggy.
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Make extra caramel. Six tablespoons of butter and a full cup of brown sugar make a gooey, deep topping that soaks into the cake instead of a thin glaze.
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Use buttermilk in the batter. Its tang cuts the sweetness, and it makes a tender, fine crumb that holds the juicy topping.
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Rest it for just three minutes. Long enough for the caramel to settle, short enough that it stays liquid. Wait longer and the sugar glues the cake to the pan.
What you need
the stars of the show
- Unsalted butter6 tablespoons
- Packed light brown sugar1 cup
- Canned pineapple rings7 slices
- All-purpose flour1 cup
- Granulated sugar¾ cup
- Buttermilk½ cup
- Eggs2 large
- Vanilla extract½ teaspoon
Topping
Cake
tap each one as it goes in. no double-salting.
Steps
go slow. the good part can’t be rushed.
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Heat the oven
Set a rack in the center and heat the oven to 350°F. Drain the pineapple and lay the rings on paper towels. Blot the tops too.
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Make the caramel
Put the 6 tablespoons butter in a 9-inch oven-safe skillet or a 9×2-inch cake pan. Melt it in the oven or over low heat, then tilt the pan to coat the sides. Sprinkle the brown sugar evenly over the bottom.
Cast iron works well and holds heat. A 9×2-inch cake pan works too.
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Arrange the fruit
Set one pineapple ring in the middle and six around it, pressing them into the sugar. Put a cherry in the center of each ring and the rest in the gaps. Don't stir.
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Mix the batter
Whisk the flour, sugar, baking powder, baking soda and salt in a large bowl. Add the softened butter and 6 tablespoons of the buttermilk, then beat on low speed until moistened and on medium for 1½ minutes. In a small bowl, whisk the eggs with the remaining buttermilk and the vanilla.
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Add the eggs
With the mixer on medium, add the egg mixture in 3 parts, beating about 20 seconds after each and scraping the bowl. The batter will be thick and smooth.
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Spread and bake
Spoon the batter over the fruit in blobs, then spread it gently to the edges without moving the rings. Bake until a toothpick in the center of the cake comes out clean, 35 to 40 minutes.
If the top browns too fast, lay foil loosely over it for the last 10 minutes.
About 38 min. Cook mode has a timer for this step.
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Rest and flip
Run a knife around the edge. Let the cake rest for 2 to 3 minutes. Set a large plate over the skillet, hold both firmly with oven mitts, and flip. Lift off the skillet. Nudge any stray fruit back with a fork and spoon on any caramel left behind.
Wear mitts and flip over the sink or a rimmed tray. The caramel is hot.
About 3 min. Cook mode has a timer for this step.
Good to know
read this before somebody asks for seconds
- Fresh pineapple works. Slice it ⅓ inch thick and sear it 2 minutes per side in a hot skillet first to cook off some moisture.
- Cherries are optional. Leave them out and the cake is just as good.
- You can serve it warm or at room temperature. Warm with vanilla ice cream or homemade whipped cream is the usual move.
- Storage. Cover and keep at room temperature for 1 day, or refrigerate for up to 4 days. Warm slices 15 seconds in the microwave so the caramel loosens.
Questions, answered
asked and answered at the kitchen counter
How do I keep my upside-down cake from sticking?
Melt the butter in the pan and coat the sides, loosen the edge with a knife and flip after 2 to 3 minutes. If any fruit sticks, press it back on the cake. It will blend right in.
Can I use fresh pineapple?
Yes. Slice it into rings about ⅓ inch thick and sear it briefly in a hot skillet to cook off some of the juice, then pat dry before arranging.
Can I bake this in a regular cake pan?
Yes. A 9×2-inch round pan works. Melt the butter in the oven, add the sugar and fruit in the pan, and bake the same time.
Why did my pineapple upside-down cake come out soggy?
The fruit wasn't dried. Blot the rings and cherries well on paper towels so the topping caramelizes instead of steaming the cake.
What can I use instead of buttermilk?
Yes. Stir 1½ teaspoons lemon juice into ½ cup of milk and let it sit for 5 minutes. Plain yogurt thinned with a splash of milk also works.
From the table
Made it? I want the full report: first bite, best compliment, and who tried to take the leftovers home.
Made it?
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Published October 29, 2026.