There’s something magical about flipping a cake. Maybe it’s the suspense. Maybe it’s the reveal. Either way, this Pineapple Upside Down Skillet Cake never fails to steal the show. Golden pineapple slices, caramelized brown sugar, and a buttery vanilla cake that melts in your mouth—it’s comfort, nostalgia, and dessert heaven all in one pan.
I’ve made this recipe countless times, and each time I hear that little sizzle when the butter hits the cast iron skillet, I know something delicious is about to happen. So grab your skillet, and let’s get baking.
Why You’ll Love This Skillet Pineapple Upside Down Cake Recipe
- One pan wonder: Everything cooks in the skillet—from caramelizing the sugar to baking the cake.
- Old-school charm: This dessert feels like something Grandma might’ve pulled from the oven on a Sunday afternoon.
- Irresistibly moist: The brown sugar syrup seeps into the cake, keeping every bite tender and sweet.
- That caramelized edge: The best part! The iron skillet gives the cake a crisp golden crust that you just don’t get from a regular pan.
Ingredients You’ll Need
For the topping:
- ¼ cup unsalted butter
- ½ cup packed brown sugar
- 6–8 pineapple slices (fresh or canned, drained well)
- 6–8 maraschino cherries (optional, but I love that pop of color)
For the cake:
- 1½ cups all-purpose flour
- 1½ tsp baking powder
- ¼ tsp salt
- ½ cup unsalted butter (softened)
- ¾ cup granulated sugar
- 2 large eggs
- 1½ tsp vanilla extract
- ½ cup milk (room temperature)
Step-by-Step: Pineapple Upside Down Cake in Cast Iron Skillet
1. Melt and caramelize
Place your cast iron skillet (I use a 10-inch) over medium heat. Melt ¼ cup butter, then stir in the brown sugar. Let it bubble gently until it looks glossy and smells like toffee—about 2 minutes.
Turn off the heat. Arrange your pineapple slices in a neat circular pattern. Add a cherry in the center of each ring if you’re feeling classic.
2. Whip up the batter
In a bowl, whisk together flour, baking powder, and salt. In another bowl, cream butter and sugar until fluffy. Beat in eggs and vanilla.
Gradually mix in the dry ingredients, alternating with milk. Don’t overmix—it should be smooth but not heavy.
3. Assemble
Pour the batter over your caramelized pineapple topping. Smooth it out gently with a spatula so it covers everything evenly.
4. Bake
Bake in a preheated oven at 350°F (175°C) for 35–40 minutes, or until a toothpick inserted into the center comes out clean. You’ll see the edges turn beautifully golden brown. That’s when you know it’s ready.
5. The flip
This is the moment of truth. Let the cake cool for 5 minutes, then run a knife around the edges. Carefully invert it onto a serving plate. Take a deep breath, lift the skillet… and there it is. A perfect upside down pineapple cake with shiny pineapple rings and syrupy glaze.
Tips for the Best Pineapple Upside Down Cake
- Use a cast iron skillet. It conducts heat evenly, giving that deep caramel color and crispy edge.
- Don’t skip the rest time. A few minutes after baking helps the topping set before flipping.
- Fresh vs. canned pineapple: Both work great. Just make sure to pat them dry. Too much juice makes the topping runny.
- Add a twist: Sprinkle a pinch of cinnamon in the caramel or use a splash of rum for a tropical kick.
Serving Ideas
This cake’s amazing on its own, but here are some fun pairings:
- A scoop of vanilla ice cream that melts into the warm caramel.
- A dollop of whipped cream and a drizzle of the syrup that pools around the edges.
- Or just a fork and a quiet corner—because sometimes, you deserve that.
Storage & Make-Ahead Tips
- Fridge: Store leftovers in an airtight container for up to 3 days.
- Reheat: Warm a slice in the microwave for 15 seconds to bring back that soft, buttery texture.
- Freeze: You can freeze individual slices for up to a month. Just wrap them tightly and thaw before serving.
Why a Cast Iron Skillet Works Best
There’s a reason this is called an Iron Pineapple Cake by old-school bakers. Cast iron holds heat like a dream, which helps the brown sugar caramelize evenly without burning. It also gives your skillet cake that slightly crisp, buttery crust that regular baking dishes can’t match.
If you don’t have one, don’t worry—you can bake this pineapple upside-down cake in a baking dish or even a deep pie pan. Just keep an eye on the edges, since non-iron pans can cook a bit faster.
My Handwritten Pineapple Upside Down Cake Recipe
I still keep an old recipe card tucked inside my kitchen drawer—a little smudged, slightly stained with butter, and written in my grandmother’s handwriting. She made this upside down pineapple cake every summer, using her trusty cast iron skillet and fresh pineapple slices from the market.
Every time I make it now, I think of that old note and how food has a way of carrying memories. Maybe you’ll start your own handwritten version after this one too.
Pineapple Upside Down Skillet Cake
Ingredients
Method
- Preheat oven to 350°F (175°C). Place your 10-inch cast iron skillet on medium heat. Melt ¼ cup butter and stir in brown sugar until it turns glossy and bubbly. Turn off heat. Arrange pineapple slices over the caramel and place a cherry in each center.
- In one bowl, whisk together flour, baking powder, and salt. In another bowl, cream butter and sugar until light and fluffy. Add eggs one at a time, then mix in vanilla. Alternate adding dry ingredients and milk until you get a smooth batter.
- Pour the batter evenly over the caramelized pineapple in the skillet. Smooth the top with a spatula. Bake for 35–40 minutes or until golden and a toothpick comes out clean.
- Let the cake cool for about 5 minutes. Run a knife around the edges, place a plate on top of the skillet, and carefully flip it over. Lift the skillet to reveal your glossy caramelized pineapple top.
- Serve warm with vanilla ice cream, whipped cream, or just as is. Every bite is buttery, tangy, and sweet all at once.
Notes
- Let the cake rest for a few minutes before flipping so the topping sets.
- Pat dry the pineapple slices to prevent a soggy topping.
- If using fresh pineapple, slice it thin for even cooking.
- For a twist, add a dash of cinnamon or a splash of dark rum to the caramel.
- The cast iron skillet gives the best crust, but you can use a heavy ovenproof pan if needed.
FAQs About Pineapple Upside Down Cake
Q1: Can I use fresh pineapple instead of canned?
Yes! Just make sure to slice it thin and dry it well before adding to the skillet.
Q2: What if I don’t have a cast iron skillet?
You can use a heavy baking dish or ovenproof pan. Just make sure it’s deep enough for the caramel and batter.
Q3: Can I make this pineapple upside-down cake in advance?
Definitely. Bake it a day before and warm it slightly in the oven before serving—it tastes even better the next day.
Q4: How do I prevent the topping from sticking?
Use enough butter and make sure to flip the cake while it’s still warm. Waiting too long can cause the caramel to harden.
Q5: What makes this the best pineapple upside down cake?
The secret’s in the skillet! The cast iron caramelizes the sugar evenly, locks in moisture, and gives that irresistible golden crust.
Final Thoughts
This Pineapple Upside Down Skillet Cake is more than dessert—it’s a slice of nostalgia with every bite. It’s proof that the simplest ingredients can create something truly memorable. So dust off that cast iron skillet, grab those pineapple slices, and bake something sweet tonight.
Because sometimes, life tastes a little better upside down.
