There’s nothing like pineapple upside down cake made from scratch.

Pineapple Upside Down Cake

I like to skip the canned and use fresh pineapple slices, classic maraschino cherries that I nestle into melted butter and brown sugar and pour a simple, moist buttermilk cake batter over top.

If you can’t tell, pineapple upside down cake, is one of my favorites.

I decided to make pineapple upside down cake because it reminds me of spring. Because I love the brown sugar soaked pineapple. And also, because I woke up to a bright and sunny Saturday morning. The sky was this cloudless, clear cerulean blue and it was that kind of day where you either spring clean your entire house form top to bottom or you make a mess in the kitchen. I went for the latter and made a cake.

And I’m glad that I did because it has rained (or snowed) just about every single day thereafter. It is/was spring break, and what a year to skip and not go on vacation to somewhere warm. So instead, the girls and I did some shopping, we went to a late night movie to see Beauty and the Beast. We went to lunch at one of our favorite spots and binge watch a few series on Netflix. It was a week of hanging out with limited working.

It was great.

Pineapple Upside Down Cake

If you were to ask me, Pineapple upside down cake is deceiving. It looks like a complicate and timely cake to make, but it really isn’t so bad. In fact, I whipped this up in under 20 minutes and slid it into the oven to bake. 35 to 40 minutes later I had this mouthwatering, stunningly retro cake on the counter. After I inverted the cake onto a cake stand, so it could cool a smidge, I quickly threw whipped heavy cream, vanilla and powdered sugar for some homemade whipped cream and brewed some coffee.

What’s better than coffee with cake?

Pineapple Upside Down Cake ingredients

To Make This Pineapple Upside Down Cake You Will Need:

  • unsalted butter, melted (divided)
  • light brown sugar
  • dark brown sugar
  • fresh pineapple slices
  • maraschino cherry
  • unbleached all-purpose flour
  • granulated sugar
  • baking soda
  • kosher salt
  • low-fat buttermilk
  • eggs
  • whipped cream

You can either use fresh or canned pineapple. I personally prefer fresh, but do what you want.

melted butter in cake pan

Preheat your oven to 350℉ (or 180℃).

Melt a stick of butter in a small sauce pan. Measure out 1/4 cup and pour it into a 9-inch cake pan. Use a pastry brush to use a little of that butter and brush the inside of the cake pan.

brown sugar in cake pan.

pineapple and cherries

Sprinkle 1/4 cup light brown sugar in the center of the cake pan and sprinkle 1/4 cup dark brown sugar around the outside perimeter. Arrange 7 slices of pineapple on top of the brown sugar and place 13 cherry halves in the center and in the spots around the edge, then set off to the side.

dry ingredients in mixing bowl with whisk

Whisk the 2 cups of flour, 1 cup sugar, 1 teaspoon of baking soda and 1/2 teaspoon of kosher salt.

add eggs, buttermilk and pineapple juice

Pour in the buttermilk (if using fresh pineapple I add about 1/4 cup fresh pineapple juice plus 3/4 cup buttermilk).

pour in melted butter

Whisk to combine while pouring in the remaining 1/4 cup of butter.

whisk to combine

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

spoon over pineapples and cherries

Next, use a rubber spatula and spoon the cake batter onto the pineapple and cherries.

smooth top of batter and bake

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

baked Pineapple Upside Down Cake

Bake in the lower third of your oven (or lowest rack if you have a small oven, like me) for 30 to 40 minutes or until a cake tester comes out clean and with only a few crumbs attached.

Pineapple Upside Down Cake

Allow the cake to rest in the pan for 10 minutes before inverting it onto a cake plate or stand.

Pineapple Upside Down Cake

See?! SO incredibly easy and it is out of this world delicious. The pineapple are so tender and sweet and the brown sugar is glazed over every square inch. Serve with a dollop whipped cream or scoop of vanilla ice cream.

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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!

Pineapple Upside Down Cake

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Yield: 12 servings

Homemade Pineapple Upside Down Cake

There's nothing like homemade pineapple upside down cake made from scratch. Fresh pineapple, classic maraschino cherries and a moist buttermilk cake.

Ingredients

  • 1/2 cup unsalted butter, melted (divided)
  • 1/4 cup light brown sugar
  • 1/4 cup dark brown sugar
  • 7 slices fresh pineapple
  • 13 maraschino cherry, halves
  • 2 cups unbleached all-purpose flour
  • 1 cup sugar
  • 1 teaspoon baking soda
  • 1/2 teaspoon kosher salt
  • 1 cup low-fat buttermilk
  • 2 eggs
  • whipped cream, for serving

Instructions 

  • Preheat your oven to 350℉ (or 180℃).
  • Position your oven rack into the lower third or very bottom of your oven. (my oven is small, so I put it on the bottom most spot.)
  • Melt a stick of butter and pour 1/4 cup (half) of it into the bottom of a 9-inch round cake pan. Use a pastry brush to brush a little of the butter around the inside of the pan.
  • Crumble and sprinkle the light brown sugar in the center of the pan, then sprinkle the outer parameter with the dark brown sugar.
  • Arrange the pineapple on top of the sugar, dot with the cherry halves and set aside for now.
  • In a large bowl, combine the flour, sugar, baking soda and salt. Pour in the buttermilk*, crack in the eggs and whisk while pouring in the remaining 1/4 cup of melted butter.
  • Once all the ingredients are combined, spoon the cake batter over top of the pineapple and smooth the top out with an offset spatula.
  • Bake in the lower third of your oven (or lowest rack if you have a small oven, like me) for 30 to 40 minutes or until a cake tester comes out clean and with only a few crumbs attached.
  • Allow the cake to cool for 10 minutes in the pan before inverting it onto a cake plate or stand.
  • Serve slightly warm cake with a dollop of homemade whipped cream.
Serving: 1serving, Calories: 295kcal, Carbohydrates: 51g, Protein: 4g, Fat: 9g, Saturated Fat: 5g, Polyunsaturated Fat: 1g, Monounsaturated Fat: 2g, Trans Fat: 1g, Cholesterol: 48mg, Sodium: 224mg, Potassium: 132mg, Fiber: 1g, Sugar: 34g, Vitamin A: 317IU, Vitamin C: 24mg, Calcium: 50mg, Iron: 1mg

Pineapple Upside Down Cake