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

1. 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.
2. 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
3. Don’t use a pan too small for this cake or it will overflow – a pan no smaller than 9 inches will work great.

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Peach Raspberry Cobbler

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Easy Banana Cake