This beautiful classic Pineapple Upside-down Cake bakes perfectly in a cast iron skillet. With its crispy golden brown sweet edges and sweet pineapple caramelized top, this cake is a huge hit and delicious taste treat.
It stays moist and decadent for days but is at its absolute best flavor shortly after baking. If you are a big pineapple fan like me. you must try pineapple casserole, pineapple salsa, and pineapple fried rice.
Ingredients Needed
- Cake flour: or all-purpose flour, but the cake flour produces a more tender crumb
- Leaveners: baking powder and baking soda
- Salt: just a touch
- Butter: unsalted or salted (if using salted, eliminate the added salt)
- Sugar: granulated and light brown sugar
- Eggs: large ones
- Vanilla extract: pure one, please
- Milk: 2% or whole is best
- Pineapple: juice and rings
- Maraschino cherries: or bing cherries, pitted and halved
How to Make Pineapple Upside-Down Cake
This is the nutshell version. See the recipe card below for the full list of ingredients and instructions.
Whisk together the flour, baking powder, baking soda, and salt in a medium bowl. Set it aside for a few minutes. Using a stand mixer or a handheld mixer on medium speed in a large bowl, cream the butter and sugar together for about 2 minutes.
Reduce the speed to low, add the eggs one at a time, mixing just until incorporated, and then add the vanilla extract.
Now, add the dry mixture to the wet mixture in several increments, alternating between the pineapple juice and the milk. Mix just until combined scraping down the bowl and beater as needed.
Meanwhile, melt butter in an 11-inch or 10-inch cast iron skillet in the oven. Sprinkle in the brown sugar as evenly as possible. Top with a single layer of pineapple slices, and fill the cored holes with maraschino cherries.
Gently pour the cake batter over the top and bake the cake in the oven for 30 minutes. Then, tent loosely with aluminum foil. Bake for another 10-15 minutes until a toothpick inserted in the center comes out clean.
Remove from the oven and let the cake cool for 10 minutes before inverting it onto a serving platter.
Recipe Tips
- If you do not have a cast iron skillet, you can make this recipe in a 9 or 10-inch cake pan as long as it is 2 inches deep.
- You can use all-purpose flour, but cake flour produces a more tender crumb.
- Get the canned pineapple in juice, not the one in syrup.
- Arrange the pineapple slices and pitted maraschino cherries as pictured above.
- Blot and dry the maraschino cherries with paper towels to keep them from bleeding through the cake.
- Carefully invert the cake onto a serving plate after 10 minutes. This is the perfect time to flip it, so stick with it. If you go too soon, the cake might fall apart, and if you wait much longer, it will stick.
- Cool the cake for 2-3 hours before slicing it with a sharp knife to prevent the slices from falling apart.
Frequently Asked Questions
You can use fresh pineapple. Core the pineapple and cut it into 1/4-inch slices.
Cover and store this cake in the refrigerator for up to 3 days or freeze for up to 3 months.
Yes, if well wrapped, you can freeze pineapple upside down cake for up to 3 months. Wrap with two layers of plastic wrap and one layer of aluminum foil. Thaw overnight in the fridge. Store the cake in the fridge
More Cake Recipes
Best Pineapple Upside Down Cake
Ingredients
Cake
- 1 ½ cups cake flour
- 1 teaspoon baking powder
- ¼ teaspoon baking soda
- ¼ teaspoon salt
- ½ cup unsalted butter softened to room temperature
- ¾ cup granulated sugar
- 2 large eggs room temperature
- 1 teaspoon vanilla extract
- 2 tablespoons milk
- ½ cup pineapple juice from the can of pineapple
Topping
- ¼ cup unsalted butter
- ⅔ cup packed light brown sugar
- 1 20-ounce can pineapple rings (reserve ½ cup pineapple juice)
- 19 maraschino cherries
Instructions
- Preheat the oven to 350 degrees. Grease a 10 or 11-inch cast iron skillet with vegetable shortening.
- In a medium bowl, whisk together the flour, baking powder, baking soda, and salt. Set it aside for a few minutes.
- Using a stand mixer or a handheld mixer on medium speed, cream the butter and sugar together for about 2 minutes. Reduce the speed to low and add the eggs one at a time, mixing just until incorporated. Mix in the vanilla extract.
- Add the flour mixture in several intervals alternating with the pineapple juice and the milk. Mix just until combined scraping down the bowl and beater as needed.
- Meanwhile, melt the butter in a 10 or 11-inch cast iron skillet in the oven. It only takes about 5 minutes, so keep an eye on it. Sprinkle in the brown sugar as evenly as possible. Top with a single layer of pineapple slices and fill in the spaces with maraschino cherries.
- Gently pour the cake batter over the top and bake the cake in the oven for 30 minutes. Then tent the pan loosely with aluminum foil. Bake for another 10-15 minutes until a toothpick inserted in the center comes out clean.
- Cool the cake in the pan for 10 minutes. Then carefully invert onto a serving plate. Let the cake cool for 2-3 hours before slicing and serving.
Notes
- If you do not have a cast iron skillet, you can make this recipe in a 9 or 10-inch cake pan as long as it is 2 inches deep.
- You can use all-purpose flour, but cake flour produces a more tender crumb.
- Get the canned pineapple in juice, not the one in syrup.
- Arrange the pineapple slices and pitted maraschino cherries as pictured above.
- Blot and dry the maraschino cherries with paper towels to keep them from bleeding through the cake.
- Carefully invert the cake onto a serving plate after 10 minutes. This is the perfect time to flip it, so stick with it. If you go too soon, the cake might fall apart, and if you wait much longer, it will stick.
- Cool the cake for 2-3 hours before slicing it with a sharp knife to prevent the slices from falling apart.
Nutrition
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Sandy V
Love your recommendation for cake flour, even though it’s something I never have on hand. (I love to cook, but I don’t bake a lot as it’s just the two of us and it would be all too easy to overindulge.) I’ve made pineapple upside-down cake in a skillet before and it’s been good but not great…always feel it’s a bit “coarse.” I’m sure the cake flour would make a huge difference. Thanks for sharing.
Beth Pierce
My pleasure, Sandy! Enjoy!