This pineapple upside-down cake has a glossy brown-sugar caramel topping studded with pineapple rings and Maraschino cherries and a tender, buttery cake underneath — sticky-sweet on top with a soft, fine crumb below.
It comes together in about 20 minutes of prep and is ready in roughly 1 hour total, serving 8; serve slices warm or at room temperature, ideally with a scoop of ice cream or a dollop of whipped cream.
Why You’ll Love This Cake
A showstopping retro dessert that’s easier than it looks: the brown-sugar caramel and fruit do the dramatic work while the cake stays reliably tender. The method is straightforward, and this version works in either a 9-inch pan or a cast-iron skillet.
This recipe gives you the technique for a reliable caramelized top and an easy inversion — follow the toothpick doneness check and the resting step for the best results.
Ingredients You’ll Need
How to Make the Cake
- Pour the melted butter into cake pan or skillet.
- Sprinkle the brown sugar over the melted butter and then top with the pineapple slices, then place cherries in the centers of the rings and in the open spaces.
- Preheat the oven to 350°F.
- In a medium bowl, whisk together the flour, baking powder, and salt. Set aside.
- Using a stand mixer, or a hand mixer with a large bowl, cream the sugar with the butter, by mixing on medium until slightly fluffy and pale in color, about 3 to 4 minutes. Scraping down the sides of the bowl a couple of times.
- Whisk in the eggs, pineapple juice, and vanilla extract.
- With the mixer running, add half of the flour mixture, once incorporated, add half of the milk. Once incorporated repeat with remaining flour and then milk. Mix until fully combined. The batter will be somewhat thick.
- Use a spatula to help pour the batter into the prepared pan and gently spread over the pineapples and cherries.
- Bake for 45 minutes, or until a toothpick comes out clean when stuck into the center of the cake.
- Let rest for 10 minutes, and then invert the cake on top of a cake stand or serving plate.
- Slice and serve warm or at room temperature. Great with ice cream or whipped cream!
Caramel Topping Tips
A glossy caramel top depends on even melted butter plus the brown sugar melting smoothly. Tilt the pan to distribute the melted butter before sprinkling the brown sugar so the sugar melts into the butter rather than clumping.
- Use light brown sugar for a softer, saucier caramel; dark brown will be more molasses-forward.
- If your sugar looks dry after arranging pineapple, gently press rings into the sugar so they contact the butter.
Skillet vs 9-inch Pan
A cast-iron skillet gives a rustic, well-browned edge and can produce excellent caramelization, but a 9-inch cake pan with 2-inch sides is often easier to invert cleanly because the sides release more predictably.
If you want a skillet-ready dessert and a similar one-pan presentation, see this related skillet dessert for inspiration: Friendsgiving 2017: Pumpkin Skillet Cobbler.
- Use a skillet for deeper browning and a pan for easier inversion and cleaner edges.
- Either pan works; simply follow the 10-minute rest and careful flip to release the cake.
Fresh vs Canned Pineapple
Canned pineapple rings are convenient and typically packed in 100% pineapple juice, which supplies both flavor and moisture to the batter. Fresh pineapple works well but tends to be less juicy and may require extra pineapple juice in the batter.
- If using fresh pineapple, plan to add a little extra pineapple juice to reach the same moisture balance.
- Canned slices give consistent size and sweetness; pat fresh rings dry if they’re excessively wet so the caramel forms properly.
Troubleshooting & Tips
Inversion safety: Let the cake rest exactly 10 minutes before inverting; a too-hot pan will spill caramel, and a too-cold cake can stick. Have your serving plate ready and use oven mitts for a confident, single smooth flip.
Batter handling: The batter is somewhat thick; use a sturdy rubber spatula or the back of a large spoon to spread it evenly over the pineapple without disturbing the fruit placement.
Toothpick doneness test: Insert a toothpick into the center: if no wet batter (not just crumbs) sticks, the cake is done. If wet batter remains, bake another 5–10 minutes and check again.
Reheating and serving: This cake is best served warm soon after baking but reheats nicely: microwave single slices briefly (10–15 seconds) to warm through before serving with ice cream.
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Final Notes
This classic upside-down cake rewards a little attention to the caramel and a confident inversion — follow the toothpick test and resting step for consistent success. Leftovers keep well at room temperature and are easily refreshed in the microwave for a minute before serving.
Classic Pineapple Upside-Down Cake
Equipment
- ▢9-inch cake pan with 2-inch side, or 9 or 10-inch cast-iron skillet
Ingredients
- 6 tablespoon unsalted butter melted
- 2/3 cup light brown sugar
- 8 pineapple rings canned or fresh
- Maraschino cherries
- 13/4 cup all-purpose flour sifted
- 11/2 teaspoon baking powder
- 1/4 teaspoon Kosher salt
- 3/4 cup unsalted butter 1½ sticks, softened
- 1 cup sugar
- 2 large eggs
- 1/4 cup pineapple juice
- 1 tablespoon vanilla extract
- 1/2 cup whole milk
Instructions
- Pour the melted butter into a 9-inch cake pan or cast-iron skillet.
- Evenly sprinkle the light brown sugar over the melted butter, then arrange the pineapple rings on top and place Maraschino cherries in the centers of the rings and in any open spaces.
- Preheat the oven to 350°F.
- In a medium bowl, whisk together the all-purpose flour, baking powder, and Kosher salt; set aside.
- In a large mixing bowl using a stand mixer or hand mixer, cream the sugar with the softened unsalted butter on medium until slightly fluffy and pale in color, about 3 to 4 minutes, scraping down the sides of the bowl as needed.
- Whisk in the eggs, pineapple juice, and vanilla extract until combined.
- With the mixer running on low, add half of the flour mixture, mix until incorporated, then add half of the milk. Repeat with the remaining flour and milk and mix until fully combined; the batter will be somewhat thick.
- Use a spatula to transfer the batter into the prepared pan and gently spread it evenly over the pineapple rings and cherries.
- Bake until a toothpick inserted into the center comes out clean, about 45 minutes.
- Let the cake rest for 10 minutes, then carefully invert the cake onto a cake stand or serving plate.
- Slice and serve warm or at room temperature; optionally serve with ice cream or whipped cream.
