This beautiful classic Pineapple Upside Down Cake bakes up perfectly in a cast iron skillet. With its crispy golden brown sweet edges and sweet pineapple caramelized top, this cake is always a huge hit and delicious taste treat. It stays moist and decadent for days, but it is at its absolute best flavor shortly after it is baked.
How to Make a Homemade Pineapple Upside-Down Cake
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 in a large bowl, 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.
Now add the dry mixture to the wet 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 butter in a 10 or 11-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 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 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.
Helpful 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 ensure the slices do not fall apart.
- Cover and store this cake in the refrigerator for up to 3 days or freeze for up to 3 months.
Can you freeze Pineapple Upside Down Cake?
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 Recipe
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 ensure the slices do not fall apart.
- Cover and store this cake in the refrigerator for up to 3 days or freeze for up to 3 months.
Nutrition
On the hunt for more delicious recipes? Follow Small Town Woman on Facebook, Pinterest, and Instagram.
https://www.smalltownwoman.com/wp-content/uploads/2019/05/Beth-1.pdf
Sue
Fabulous! Love those chewy, caramelized edges. Thank you for a great recipe!
Beth Pierce
Thanks, Sue so glad that you liked the pineapple upside down cake.
Neely Moldovan
Oh my god this looks so good! One of my favorites!
Monica
Just by the look of it I can imagine that I am in for a treat with this pineapple upside-down cake recipe! The visuals alone are mouthwatering, and I can imagine how delicious it must taste.
Zab
This recipe was so delicious! This will be on my rotation list as it was that good!
Shane
This pineapple upside down cake was so delicious and fluffy! My family loved it. It was a real blockbuster here!
Ntensibe Edgar
Wwwooowwwww….I have seen this kind of cake before, in a magazine but had never known it’s actual name. It looks so pretty and since pineapple is a good friend of mine, I look forward to giving it a try!
Beeb
This pineapple upside-down cake makes a fun centrepiece for afternoon tea and brings back many childhood memories.
Beth Pierce
Food can be so nostalgic!
Stephanie
Yum! This is such a light and fluffy pineapple upside down cake. And it looks so nice on my dessert table.
Beth Pierce
Thanks Stephanie! So glad that you enjoyed it.
Heather
I’m so excited to try this recipe. It’s been way too long since I’ve had a pineapple upside down cake.
Beth Pierce
Thanks, Heather! Enjoy!
Stephanie
This is one of my favorite cakes! I make mine almost the exact same as yours. The pineapples are delicious in the cake and keep it so moist!
Debbie
This pineapple upside down cake is delicious. Everyone at my summer barbecue thoroughly enjoyed it.
Tina Basu
wow this looks super amazing. My son would love this. I have to give it a try.
Zadie
This recipe is so delicious! I love how it cooks in the skillet. This will be my go to recipe for pineapple upside down cake in the future!
Catalina
Great pineapple cake recipe. It turned out perfect and whole family loved it.
Sandra
This is my favorite way to enjoy pineapples!! So amazing and always comes out perfectly!
Marysa
I have never made something like this before. Sounds like a unique dessert and it would be fun to try. Makes for a fun summer dessert idea!
Erin
Looks beyond delicious! Can’t wait to make this!
Jupiter Hadley
Pineapple upside down cake is such a classic cake! I love how good it presents Thank you for sharing your recipe.
Jack
Great cake. It reminds me of my Mom’s pineapple upside down cake. Crisp edges with a tender moist crumb. Thank you for sharing!
Tammy
I love pineapple upside down. It’s such a fun and delicious summer dessert…I haven’t had one in ages so I am really looking forward to trying this recipe ^_^
karen
This cake wass out of this world omg….It cooked up perfect in my cast iron skillet. This is my new go to recipe for pineapple upside down cake!
Lavanda
I can already imagine the sweet aroma and the mouthwatering taste. Can’t wait to surprise my loved ones with this scrumptious treat!
Nyxie
I love an upside down cake. I’ve had something similar before with pineapples and cherry’s and I have to say it was gorgeous!
Barbie
It’s been a while since I’ve had pineapple upside down cake – I remember my mom used to make it for me when I was a kid and I loved it so much. It’s so delicious!
Alita
This was so delish. it’s no wonder why it has been a must-make favorite for generations.
Beth Pierce
Thanks, Alita! So glad that you liked it!
Alita
Yes, My family loved it too and we usually have it for afternoon tea.
Brianne
I wowed our friends and family with this classic pineapple upside-down cake. They loved it! Thank you so much!
abzstylz
I haven’t had upside down cake in so long! My grandmother made it a lot when I was growing up, and regret not getting her recipe before she passed. Your cake looks amazing, so will be trying!
CInny
That looks like a dessert my son would love. I think I’ll try to make this one day.
Ned
Ooohhhh….this is a new variation of pineapple cake to me, I must say it has got a unique design and appearence, to what I am used to, at least. Thanks for sharing this recipe.
Brittney
I love how easy your recipes are to follow and that you include many photos. I’ve never considered making pineapple upside down cake, but your easy recipe has me wanting to try this out really soon.
Beth Pierce
Thanks Brittney! Enjoy!
Mandy
Yummy! Brings back childhood memories – this was one of my grandma’s favorite sweets to have on summer holidays.
Beth Pierce
Good choice!
Stephanie
Who doesn’t love a good upside down pineapple cake! This is a great recipe and one more reason to break out my cast iron skillet.