Pineapple Upside Down Cake – Fluffy vanilla cake topped with brown sugar pineapple slices
During my pregnancy last year, I was eating lots of fruit. I couldn’t buy it fast enough so I start buying it in cans so we always had some on hand. Pineapple was one of those fruits I loved to eat from a can – it’s less acidic that way and it’s fun for me to eat in slices.
One day, my husband casually suggested I use some of that pineapple to make a pineapple upside down cake. It wasn’t a dessert typically on my radar because, honestly, I don’t think I’ve ever had it before. And if I did, it clearly wasn’t a memorable one.
However, for my husband, this dessert is right up my his flavor alley – brown sugar, cooked fruit, and vanilla cake. It’s also super simple to make, which I appreciated (read as: I was pregnant and tired so I’m not slaving away on anything). So why not try out this dessert? I’m always looking to try new recipes, especially during the pandemic when there was very little for us to do.
The cake was a huge success so I just had to recreate it for you all here. It also freezes really well so if you have a small family like mine, you can make during the week and freeze leftovers for another time!
Before we get into the recipe, here are some more photos of the gorgeous cake!
When looking for a great recipe to use for pineapple upside down cake, I wanted only one thing: a vanilla cake. There were a few recipes I found that use pineapple juice in their cake. But I wanted the topping to be all pineapple with a more subtle vanilla cake underneath.
To ensure the cake was everything I wanted, I used a recipe from one of my blogger friends, Sugar Spun Run. She tests her recipes thoroughly and prides herself on authenticity so I knew her recipe would be stellar.
And it certainly was! The cake was super moist and the topping was caramelized brown sugar perfection. We couldn’t stop eating it!
How is this cake made
Pineapple upside down cake it exactly that – you make the cake with the intention of flipping it upside down after it bakes. The brown sugar and butter caramelize to create a topping that holds the pineapple and cherries right in place.
To create the cake, first we layer in the topping, making sure the pineapple slices are arranged beautifully under the melted butter and brown sugar.
After the pineapple is layered, it’s time to make the cake. It’s a simple cake recipe made from butter, eggs, sugar, flour, and milk. It’s also flavored with a little vanilla for a little punch.
The batter it gently spread over the pineapple slices and then the cake is baked until the center is cooked-through. It’s then cooled for no more than 10 minutes and then flipped upside down to reveal a gorgeous caramelized pineapple crusted top.
I’ve eaten this cake cooled and warm and it’s 1000% better when eaten warm. The sugar topping tastes so rich when it’s warm that it’s impossible to resist.
Tips & Tricks
- Do not let the cake cool completely before turning onto a plate. When the topping cools, it will stick to the pan like glue. Therefore, it’s important to flip the cake when warm.
- To have a nice look on the top of the cake, don’t overlap the pineapple slices when arranging them on the bottom of the pan
- Don’t use a pan too small for this cake or it will overflow – a pan no smaller than 9 inches will work great.
Pineapple Upside Down Cake
Ingredients
For the topping:
- 7-10 slices canned pineapple
- 7-10 maraschino cherries
- ¼ cup butter melted
- ⅓ cup brown sugar
For the cake:
- ½ cup butter unsalted, softened
- ¾ cup granulated sugar
- 2 large eggs
- 1 teaspoon pure vanilla extract
- 1½ cups all-purpose flour
- 1½ teaspoons baking powder
- ¼ teaspoon salt
- ½ cup whole milk
Instructions
- Preheat oven to 350 degrees. Grease a 9-inch cake pan or a deep dish pie pan. Line the bottom of the pan with ¼ cup melted butter and ⅓ cup brown sugar. No need to whisk together. Place slices of pineapple on top of brown sugar, trying your best not to overlap the pineapple slices. Place a Maraschino cherry in the center of each pineapple slice. Set aside.
- Add softened butter and granulated sugar to bowl of a stand mixer. Beat together with paddle attachment until light and fluffy, about 4 minutes. Add one egg, beat, add other egg, beat, and then add vanilla extract and beat.
- In a separate bowl, whisk flour, baking powder, and salt. Add half of the dry ingredients to the bowl of the stand mixer and beat just until combined. Add milk and beat just until combined. Finally, add last of dry ingredients and beat just until combined.
- Gently pour batter over the pineapple, being careful not to slide the pineapple and Maraschino cherries around. Spread into an even layer. Bake cake in preheated oven for 30 minutes. After 30 minutes, loosely cover with foil to prevent cake from browning too much. Cook for another 10-15 minutes, or until toothpick comes out clean when inserted in the center.
- Remove from oven and let cool for 10 minutes. Then, flip cake onto plate to finish cooling or serve warm with ice cream. The remaining can be frozen for up to 3 months.
Notes
Pin for later:
More recipes you’ll love:
Peach Raspberry Cobbler
Berry Crumble Pie
Easy Banana Cake
What a beautiful bright dessert perfect for the summer! This recipe was so easy to follow and the addition of the cherries were perfect. YUM!
When I was a little girl, one of my aunties used to make this cake. When I saw your pics I couldn’t stop my cravings, so I made your upside-down pineapple cake. I dream came true!
I was so happy to discover your pineapple upside -down cake recipes-I haven’t made this cake since I was a kid. Your version looks so moist and delicious-perfect for a summer treat!
Such a classic recipe with such beautiful pictures1 It’s such a fun cake that everyone loves! Growing up, this was a standard cake for every cookout and bbq. Thank you so much for sharing your recipe as it looks amazing!
This cake was delicious! The vanilla cake turned out so moist and fluffy, and the pineapple just made it over-the-top delicious. Perfect summer cake!
I thought this cake was just magical when I was growing up, and it’s nice to see this version is relatively simple and flavorful (not from a cake mix!). Can’t wait to try it.
In the past my pineapple upside down cake has been a little off. Not to say it didn’t look okay but nothing to be proud of. I followed your recipe and instructions and the cake turned out perfectly. It looked so good I served it at my book club meeting.
Your tips were very useful, my pineapple upside down cake turned out amazing! Certainly making this again!
Vanilla cake topped with pineapple, perfect combo! This is a really classic cake, and it was so good! Great way to use up some leftover cherries as well!
I have never actually had pineapple upside-down cake. For me, it’s always been one of those things you see on TV. Can’t wait to make it!
I love alllll things pineapple, and this cake is out of this world! Thanks so much for sharing the recipe!
How pretty AND delicious! It turned out perfectly and wasn’t too sweet at all! Yum!
This cake is so easy and delicious! I haven’t made one at home before this but I’ll certainly be making it again!
Such a classic cake and it looks os pretty too!
I haven’t had pineapple upside down cake for years but I want some now! Great photos and a great recipe, thanks.
Yum I love Pineapple Upside Down Cake, It was the first cake I learned how to make andI won a blue ribbon for it in Girl Scouts!
This is such a classic (that looks absolutely fabulous!) and I would love a slice right now! Very good to know that it freezes well – great suggestion!
This is the quintessential cake of my childhood cookout memories. It still brings memories of military unit functions and ceremonies.
Such a fun cake and since my birthday is approaching I definitely need to try it