Boy Bakes Treats - Pineapple Upside-Down Cake

Pineapple Upside-Down Cake

Boy Bakes Treats - Pineapple Upside-Down Cake

Firmly lodged into the American cake consciousness around the mid 1920s thanks to a recipe contest run by James Dole’s Hawaiian Pineapple Company, it's honestly not hard to see why the pineapple upside-down cake has dazzled hungry treat-lovers for decades. Juicy pineapple rings and sweet cherries coated with a sticky caramel glaze sit on top of a buttery, pineapple-infused vanilla cake — it tastes as good as it looks. And it looks spectacular.

Just quietly, it's also not that difficult to make. The fruit is baked in a sugar mixture in the bottom of the pan with the batter on top, and all it takes is a final flip at the end to produce an applause-worthy upside-down cake.

When you're procuring the pineapple, go for can with the slices in juice rather than syrup. You'll use the juice in the batter and it will also mix in with the brown sugar topping while baking, so the syrup is going to be a sweetness overload. Adding a bit of bicarbonate of soda will help tamper the acidity of the juice.

Buttermilk has been used in here to add some richness to the cake, but if you're light on, you can always use 1 tablespoon of white vinegar or lemon juice plus enough milk to measure 1 cup. Stir, then let it stand for 5 minutes.

You'll need to get the cake out of the pan pretty quickly once it's done baking, so arm yourself with some oven gloves and a plate big enough to catch the cake and any additional caramel drips. After 5 minutes, place the plate on the pan and flip it quickly. You can use the overhanging baking paper to assist as you slowly lift the cake pan off. If there are any pieces that end up sticking to the paper, that's entirely OK. Quickly patch them back on, the sauce should make them stick, and no-one will suspect a thing.

Oh, and don't write off the cherries. They're entirely optional, but they will definitely add a pop of colour if you're going for presentation marks (the redder the better), and a pop of sweetness to brighten up the delicous caramel sauce.


24 squares


30 minutes


50 minutes



  • 60 grams butter
  • 110 grams brown sugar
  • 1/2 teaspoon ground cinnamon
  • 440 grams canned pineapple slices in juice
  • 10 glace cherries (optional)


  • 300 grams self-raising flour
  • 1/4 teaspoon salt
  • 110 grams brown sugar
  • 60 grams caster sugar
  • 125 grams butter
  • 1 teaspon vanilla extract
  • 2 eggs
  • 3/4 cup buttermilk
  • 1/4 cup pineapple juice
  • 1/4 teaspoon bicarbonate soda


  1. Heat oven to 180 degrees Celsius/360 degrees Fahrenheit. Lightly grease a 22cm round or square cake tin. Line base and sides with baking paper, extending the paper 2cm above the edge for easy removal later. Leave the butter to warm to room temperature and cut into cubes.
  2. Drain the pineapple slices, reserving 1/4 cup of the juice. Blot any excess liquid off the fruit with a paper towel — the wetter the fruit, there's a higher chance that the cake could overflow or the topping could seep out when you flip the cake.
  3. Sift the flour and salt into a small bowl and set aside.
  4. In a small saucepan set over a medium heat, melt the butter, cinnamon and sugar, until the sugar has dissolved and the mixture is bubbling. Simmer for one minute, then pour the mix into your prepared tin and use a pastry brush to spread it around evenly.
  5. Arrange the pineapple slices in a single layer on top of the brown sugar mixture, halving some of the slices to fit around the edges of the pan. Add the glace cherries in the centre of the slices (or wherever you think would look best). Your aim is to cover as much surface area as you can, so there's a real fruit hit in each slice. Place the tray in the fridge while you make the batter.
  6. Cream the sugars, butter and vanilla in a large bowl with an electric mixer until light and fluffy. Add one egg at time, beating the mixture well after each addition. Scrape down the sides of the bowl with a rubber spatula as needed.
  7. Add the flour mixture and buttermilk in alternating batches, starting and ending with the flour, and stir after each addition until just combined. Gently mix in the reserved pineapple juice and bicarbonate soda.
  8. Remove your tray from the fridge. Pour and spread the batter evenly over the pineapple and caramel, pressing to the edges and smoothing the top.
  9. Bake for 45-50 minutes or until a light golden brown or a toothpick or skewer inserted into centre of the cake comes out clean. If you find the top is browning too quickly, cover loosely it with aluminium foil.
  10. Remove from oven and leave to cool in the tin on a wire rack for about 5 minutes. Place a plate on top of the tin and flip it over, then use the overhanging baking paper to separate the tin from the cake. If any of the cake sticks, dig it out, patch it back on and cover it up with some of the gooey sugar sauce. Let it cool completely at room temperature before slicing and serving.

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