Pineapple Upside Down Cake

In this classically retro homemade Pineapple Upside Down Cake, pineapple slices and maraschino cherries are baked in brown sugar and butter with a moist and spongy, vanilla buttermilk cake. Serve slices with a dollop of whipped cream and an extra cherry on top!

Pineapple upside down cake Is one of my all-time favorite cakes.

Tender pineapple slices and classic maraschino cherries baked in brown sugar and butter, topped with tender buttermilk cake. Not only is it stunning but also delicious!

Last week I decided to make pineapple upside down cake because it reminds me of spring. But mostly because I love the brown sugar and butter soaked pineapple. It was the perfect spring day, the sky was this cloudless and a crystal clear cerulean blue. A day where you either spring clean your entire house form top to bottom or you make a mess in the kitchen.

Obviously, I went for the latter.

To Make This Pineapple Upside Down Cake You Will Need:

for the pineapple layer:

• unsalted butter (melted) – Adds flavor and aids in caramelizing the pineapple layer when baking.
• light brown sugar – Lends sweetness and subtle caramel flavor.
• pineapple slices – I’ve made this with fresh and canned pineapple and have found canned is more convenient to get both the pineapple and juice.
• maraschino cherries – Add a pop of color and delicious sweet cherry flavor.

for the cake:

• unbleached all-purpose flour – This is the base for the cake batter.
• baking powder – Will create lightness in the batter, which makes it rise.
• baking soda – Reacts with the buttermilk to make these light and airy.
• fine salt – Use either sea salt or pink himalayan.
• eggs – Set out 30 minutes before using or let sit in a bowl of lukewarm water.
• buttermilk – Lends delicious tangy flavor and reacts with the baking soda for a light and fluffy cake.
• pineapple juice – Reserved from the pineapples.
• granulated sugar (white) – Lends sweetness and flavor.
• pure vanilla extract – Adds warmth and enhances the flavors in the cake.

Optional toppings for serving:

• whipped cream
• extra cherries

Preheat your oven to 350℉ (or 180℃).

Melt all the unsalted butter (1½ sticks) at once in a small sauce pan. Measure out 1/2 cup and set aside (for the cake). Using a pastry brush, brush and some of the remaining butter and brush the inside of the cake pan.

Make The Pineapple Layer:

Then, add 1/2 cup of light brown sugar to the remaining 1/4 cup of butter (still in the sauce pan) and stir until combined.

Next, pour the brown sugar and butter mixture into the buttered cake pan and spread evenly.

Place one pineapple slice in the center on top of the brown sugar mixture and arrange 11 to 12 halved pineapple slices at a slight angle around the perimeter. Then place 12 cherries in the “center” of the pineapple slices. Of course you can always nestle more into any nook or cranny if you’d like. Set this off to the side.

Make The Cake Batter:

In a large mixing bowl, measure and add 2 cups of unbleached all-purpose flour, 3/4 cup granulated sugar, 2  teaspoons baking powder, 1/4 teaspoon baking soda and 1/2 teaspoon of fine salt.

Whisk to combine and make a well in the center.

In a separate bowl or liquid measuring cup,  measure and add 2 eggs, 3/4 cup buttermilk, 1/2 cup (melted and cooled) unsalted butter, 1/4 cup pineapple juice and 1 generous teaspoon of vanilla extract.

Whisk well to combine.

Pour the buttermilk mixture into the well of the dry ingredients.

Gradually stir, to combine.

A few lumps are okay, just try not to over mix.

Spoon the cake batter on top of the pineapple and cherries.

Then use an offset spatula to smooth out the top of the cake batter.

Bake on the middle rack of  your preheated oven for 40 to 45 minutes or until a tester is inserted and. comes out clean with a few crumbs attached.

Allow the cake to cool in the pan for 20 minutes.

After 20 minutes, run a knife around the edges and carefully invert it onto a cake plate or stand.

Stunning!

Allow the cake to cool before slicing and serving.

I like to add a dollop of whipped cream and add an extra cherry on top.

How To Store Homemade Pineapple Upside Down Cake?

Once the cake has cooled completely, store in an air-tight container (linked in recipe printable) at room temperature.

How Long Will Homemade Pineapple Upside Down Cake Last?

In my opinion, it is best to enjoy this cake the day of being made.  However, if stored properly, it will last for up to 3 to 4 days.

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Enjoy! And if you give this Pineapple Upside Down Cake recipe a try, let me know! Snap a photo and tag me on twitter or instagram!

This recipe was originally posted on April 8, 2017 and has been updated with clear and concise instructions, new photography and helpful information.