The BEST Pineapple Upside-Down Cake
I used to be a pineapple upside-down cake hater…but baaaby, not after this recipe! This one has the best gooey, caramelized pineapples and a tender, moist & buttery cake that just melts in your mouth.
It took me six rounds of recipe testing to get this perfect Pineapple Upside-Down Cake.
It’s my husband’s favorite cake, (besides this ultimate chocolate cake) so I was determined to create a really good one for his birthday.
This is the recipe that converted me into a fan, because now I love pineapple upside-down cake (or at least when it’s made with this recipe), and I think you will too!
Why You’ll Love This Pineapple Upside-Down Cake Recipe
- That gooey, brown sugary, caramelized pineapple topping is showing out!
- Easy vanilla cake base with a buttery, moist crumb.
- Simple ingredients
- Tested and perfect recipe & a true family favorite.
Watch How to Make Pineapple Upside-Down Cake Step-By-Step
Come on into my kitchen and let me show you how I make this pineapple upside-down cake from start to finish.
I’ll show you exactly how to flip it out of the pan while leaving that caramelized pineapple topping perfectly in place.
Here’s What You’ll Need
Ingredients:
For The Topping
- Unsalted butter (melted)
- Light brown sugar (packed)
- Pineapple rings
- Maraschino cherries
For The Cake
- Unsalted butter
- Butter-flavored shortening (Do not substitute with plain shortening)
- Granulated sugar
- Light brown sugar
- Eggs
- Vanilla extract
- All-purpose flour
- Baking powder
- Salt
- Heavy whipping cream
- Whole milk
How to Make Pineapple Upside-Down Cake Step-By-Step
Instructions
Make the Topping
- Preheat the oven to 325 F. Move the oven rack to the middle of the oven. (Place a baking sheet on the bottom rack just in case juices from the cake bubble over a bit.)
- In a deep 9.5-inch glass pie dish, add melted butter and spread it out to cover the bottom
- Sprinkle brown sugar evenly over the butter.
- Place a whole pineapple ring in the middle of the pan.
- Slice the other pineapples in half and place the halves around the middle pineapple.
- Place a cherry in the center of each space. (Refrigerate until ready to use)11 maraschino cherries
Make the Batter
- In a large bowl, cream together butter, shortening, white sugar, and brown sugar.
- Mix in eggs and vanilla extract. Set aside.
- In a separate bowl, whisk together flour, baking powder, and salt.
- Gradually add the dry ingredients to the wet ingredients while alternating between the heavy whipping cream and milk.
- Mix just until batter is combined and fluffy; do not overmix.
- Pour batter over pineapples and carefully spread out into an even layer.
Bake
- Bake for 40 minutes.
- Then cover loosely with tented foil (to prevent further browning) and bake for another 30-35 minutes (may need shorter or longer) or until a cake tester inserted into the middle of the cake comes out clean.
- Remove from the oven and let the cake cool for about 15 minutes.
Invert The Cake!
- While the cake is still warm, place a cake stand or serving dish over the pie dish.
- Carefully flip both over in one smooth motion. (Use oven mitts since the bottom of the pie dish will be hot! (See video for detailed demonstration)
- Carefully remove the pie plate. Serve the cake warm.
Note: Don’t wait too long to flip the cake out of the pan. If it cools too much, it will stick to the pan
Mo’s Test Kitchen Tips
Use fresh pineapples. If you can get them, use fresh pineapples for the best flavor and slice them evenly. Canned pineapples work if you are not able to get fresh ones. Get the ones that are in juice and not syrup. You can also get pre-cut fresh pineapple rings in most grocery stores.
Don’t overmix the cake batter. Overmixing will cause a crumbly crumb texture
Don’t leave the cake in the pan too long. The cake must still be hot when you go to invert it. Allow it to cool in the pan for about 15 minutes only. If it gets too cool, the gooey topping will start to firm up and seal the cake to the pan.
Serve warm. Pineapple Upside-down cake is best when the pineapple topping is warm and gooey.
FAQs
How do you invert (flip over) a pineapple upside-down cake? Using a glass pie dish with handles is extremely helpful.
- Place your cake stand or serving board over the pie dish.
- Grab the handles on the pie dish and the cake stand so that you have them both pinched together. Use pot holders since the pie dish will be hot. (see video for demonstration).
- Quickly flip it over in one motion so that the pie plate is now on the cake stand.
- Very carefully remove the pie plate. This is why I ONLY bake pineapple upside-down cakes in glass dishes! I can see if anything is sticking and gently wiggle it until it releases.
Can I use all butter instead of the butter-flavor shortening? Yes, you can, but the texture will be lighter.
Can I use canned pineapples instead of fresh ones? Yes. If I can’t get fresh pineapple, I like to use Del Monte Deluxe Gold (black can). They are quick, easy, and perfectly sweet!
Why did my pineapple upside-down cake stick to the pan? This usually happens if the cake has cooled too long before flipping. Invert it while it’s still hot (about 10-15 minutes after baking).
Why is my cake dry? You likely overmixed the batter or baked it too long. Mix just until combined and cook until a toothpick inserted in the center comes out clean or with moist crumbs clinging to it.
Why is my topping water? This happens if there is too much moisture from the pineapples. Be sure to dry the pineapple slices completely with paper towels before placing them on the bottom.
Which cake pan should I use? I always use a 9.5-inch deep glass pie plate. I just love the way the glass cooks this cake without anything sticking to it. And bonus, I can see the bottom when I flip it over to ensure nothing is sticking. I’ve never cooked this cake in a cast-iron skillet or dark pan, so I can’t make any recommendations for those.
How To Store
Store pineapple upside-down cake covered in the fridge for 2-3 days. This cake is BEST eaten the same day and served hot.
For the best texture, warm individual slices in the microwave for about 10-15 seconds before serving
If you’ve been on the hunt for a really good pineapple upside-down cake with perfect gooey, hot caramelized pineapples and the most amazing buttery vanilla cake, this is the recipe!
If you try this recipe, let me know how it turns out! Grab the recipe below.
Get the Recipe:
Pineapple Upside-Down Cake
Ingredients
TOPPING
- 6 tablespoons unsalted butter melted
- ⅔ cup light brown sugar packed
- 1 20 oz. can pineapple rings (in their own juices, not syrup) (about 11 slices, dried with paper towels)
- 11 maraschino cherries
CAKE
- 4 tablespoons unsalted butter room temperature
- 4 tablespoons butter-flavored shortening (a must, don't use plain)
- ½ cup + 2 tablespoons granulated sugar
- ¼ cup light brown sugar packed
- 2 eggs room temperature
- ½ teaspoon vanilla extract
- 1½ cups all-purpose flour
- 1½ teaspoons baking powder
- ¼ teaspoon salt
- ½ cup heavy whipping cream
- ¼ cup whole milk
Instructions
Make the Topping
- Preheat the oven to 325 F. Move the oven rack to the middle of the oven. (Place a baking sheet on the bottom rack just in case juices from the cake bubble over a bit.)
- In a deep 9.5-inch glass pie plate, add melted butter and spread it out to cover the bottom.6 tablespoons unsalted butter
- Sprinkle brown sugar evenly over the butter.⅔ cup light brown sugar
- Place a whole pineapple ring in the middle of the pan.1 20 oz. can pineapple rings (in their own juices, not syrup)
- Slice the other pineapples in half and place the halves around the middle pineapple.
- Place a cherry in the center of each space. (Refrigerate until ready to use)11 maraschino cherries
Make The Cake
- In a large bowl, cream together butter, shortening, granulated sugar, and brown sugar.4 tablespoons unsalted butter, 4 tablespoons butter-flavored shortening, ½ cup + 2 tablespoons granulated sugar, ¼ cup light brown sugar
- Mix in eggs and vanilla extract. Set aside.2 eggs, ½ teaspoon vanilla extract
- In a separate bowl, whisk together flour, baking powder, and salt.1½ cups all-purpose flour, 1½ teaspoons baking powder, ¼ teaspoon salt
- Gradually add the dry ingredients to the wet ingredients while alternating between the heavy whipping cream and milk.½ cup heavy whipping cream, ¼ cup whole milk
- Mix just until batter is combined and fluffy, do not over mix.
- Pour batter over pineapples and carefully spread out into an even layer.
Time to Bake!
- Bake for 40 minutes. Then cover loosely with tented foil (to prevent further browning) and bake for another 30-35 minutes (may need shorter or longer) or until a cake tester inserted into the middle of the cake comes out clean or with moist crumbs clinging to it.
- Remove from the oven and let the cake cool for about 15 minutes only.
Time to Invert The Cake!
- While the cake is still warm, place a cake stand on top of the pie plate and carefully flip both over. (Use oven mitts since the bottom of the pie plate will be hot! See video for demonstration)
- Carefully remove the pie plate. Serve the cake warm.
Video
Notes
Mo’s Test Kitchen Tips
Use fresh pineapples. If you can get them, use fresh pineapples for the best flavor and slice them evenly. Canned pineapples work if you are not able to get fresh ones. Get the ones that are in juice and not syrup. You can also get pre-cut fresh pineapple rings in most grocery stores. Don’t overmix the cake batter. Overmixing will cause a crumbly crumb texture Don’t leave the cake in the pan too long. The cake must still be hot when you go to invert it. Allow it to cool in the pan for about 15 minutes only. If it gets too cool, the gooey topping will start to firm up and seal the cake to the pan. Serve warm. Pineapple Upside-down cake is best when the pineapple topping is warm and gooey.Nutrition
Want more perfected classic cakes? Check these out!
I love this quick and easy to make pineapple upside down cake! I’ve made this cake 4 times already for other people, the difference is I added 1/2 vanilla and 1/2 pineapple flavoring to put a little more kick of pineapple flavor in the cake.