Next-Level Pineapple Upside Down Cake

12 servings


20 minutes

active time

55 minutes

total time



½ cup (4oz/115g) butter 80

1 ¼ cups (7½oz/213g) dark brown sugar 150

1 large can (20oz/567g) sliced pineapple in juice

10-13 maraschino cherries ((stems removed))


½ cup (4oz/115g) butter, softened 80

½ cup (4oz/115g) granulated sugar 80

⅓ cup (2oz/57g) dark brown sugar 39

2 large eggs

½ cup (4floz/120ml) whole milk 84

½ cup (4floz/120ml) juice from the tinned pineapple 84

1 teaspoon almond extract

2 cups (10oz/284g) all-purpose flour 200

2 teaspoons baking powder 1 1/4

½ teaspoon salt


To Make The Caramel:

Preheat the oven to 350°F (180°C) and generously butter a 9x13-inch (23x33cm) baking pan. Set aside.

In a small saucepan over medium-low heat, combine butter and brown sugar and simmer until the sugar is dissolved in about 2-3 minutes. Pour into the prepared baking pan.

Drain the pineapple rings and reserve ½ cup (4floz/120ml) of juice. Arrange as many rings 4 x 3 or as you can fit in a single layer in the pan on top of the butter and brown sugar mixture.

Place a maraschino cherry in the center of each pineapple ring.

To Make The Cake:

In a medium mixing bowl, combine the flour, baking powder and salt, mix well and set aside.

In a large bowl cream together room temperature butter, dark brown sugar and granulated sugar until light and fluffy.

To the butter-sugar mixture, whisk in the first egg and cream it until fully incorporated. Add in the second egg and cream it until fully incorporated, too.

Then mix in the dry ingredients until it comes together and resembles bread crumbs.

Slowly stream in milk followed by the reserved pineapple juice.

At last, measure and pour in almond extract. Mix all until just combined and the batter is light and fluffy.

Carefully spread the batter over the pineapples and then bake for 35-40 minutes, until a wooden skewer inserted into the center comes out clean.

Let the cake cool for 10 minutes in the pan before inverting onto a serving tray.

This cake is best the day it is made, but you can store leftovers in an airtight container at room temperature for up to 2 days.

12 servings


20 minutes

active time

55 minutes

total time
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