Ingredients

For the Topping:

• 565g (20 oz) canned pineapple slices in juice (not syrup) (See Note 1)
• 12 – 18+ maraschino cherries (See Note 2)
• 60g (4 tbsp) unsalted butter, melted
• ½ cup brown sugar

For the Cake:

• 1½ cups all-purpose flour
• 1 tsp baking powder
• ¼ tsp baking soda (or substitute with 1 tsp baking powder)
• ¼ tsp salt
• ⅓ cup milk (full-fat or low-fat)
• ¼ cup pineapple juice (reserved from the canned pineapple)
• ¼ cup full-fat sour cream (or substitute with plain yogurt)
• 1 tsp vanilla extract (or vanilla essence)
• 115g (1 stick) unsalted butter, softened (to 18°C/64°F, See Note 3)
• ¾ cup white sugar
• 2 large eggs, at room temperature (See Note 4)
• Any leftover pineapple, chopped (See Note 1)

Instructions

Preheat the Oven:

• Set your oven to 180°C (350°F) or 160°C (320°F) if using a fan-forced oven.

Prepare the Pineapple Topping:

1. Drain & Dry the Fruit : Line a tray with paper towels and place the pineapple slices and cherries on top. Pat them dry with additional paper towels to remove excess moisture.
2. Butter the Pan : Pour melted butter into a 23cm (9-inch) round cake pan (at least 5 cm/2” deep). Avoid springform pans, as they may leak. Use a brush to spread butter evenly over the base and sides.
3. Add Brown Sugar : Sprinkle the brown sugar evenly over the bottom of the pan. Use a brush or spoon to spread it out slightly.
4. Arrange the Pineapple & Cherries : Place one pineapple ring in the center, then surround it with halved or whole pineapple slices. Add maraschino cherries as decoration, either in the center of the pineapple rings or filling any gaps.
5. Press Firmly : Gently press the pineapple and cherries into the base to ensure they make direct contact with the pan. This helps achieve vibrant colors once the cake is flipped. (See Note 5)

Prepare the Cake Batter:

1. Mix Dry Ingredients : In a bowl, whisk together flour, baking powder, baking soda, and salt.
2. Combine Wet Ingredients : In a separate bowl, mix milk, sour cream, pineapple juice, and vanilla extract until smooth.
3. Cream Butter & Sugar : In a third bowl, beat softened butter and sugar using an electric mixer on high speed for about 2 minutes, until the mixture is light and fluffy.
4. Incorporate Eggs : Add eggs one at a time, beating well after each addition.
5. Alternate Adding Dry & Wet Ingredients : Using a spatula, fold in ⅓ of the dry mixture, then mix in half of the wet mixture. Repeat this process until all the flour and wet ingredients are combined, finishing with the last portion of the dry ingredients.
6. Fold in Pineapple Pieces : If you have leftover chopped pineapple, gently fold it into the batter.

Assembling & Baking:

1. Spread Batter Over Topping : Pour the batter into the pan over the pineapple and smooth the surface evenly.
2. Bake in the Oven : Place in the oven and bake for 30 minutes. Then, cover loosely with foil and continue baking for another 15 minutes, or until a toothpick inserted into the center comes out clean.

Unmolding the Cake:

1. Cool Slightly : Remove from the oven and allow the cake to rest in the pan for 20 minutes.
2. Flip the Cake : Run a butter knife along the edges of the pan. Place a serving plate or platter on top, then confidently flip the cake over. Gently tap or shake the pan if needed, then lift it off slowly.
3. Let It Cool Completely : Allow the cake to cool fully before slicing and serving.

Recipe Notes:

1. Pineapple Selection : Use canned pineapple in juice, not syrup, as syrup makes the cake too sweet. If you have extra pineapple, chop it up and add it to the batter.
2. Maraschino Cherries : These sweet preserved cherries are often used in cocktails. They can be found at liquor stores or specialty grocery stores. Glacé cherries are a suitable substitute.
3. Butter Temperature : Ensure butter is soft but not overly warm (around 18°C/64°F). If it’s too soft, the cake may turn out dense or greasy. If your butter is warmer than 20°C/68°F, chill it briefly before using.
4. Egg Temperature : Eggs should be at room temperature for proper mixing. To quickly warm them up, place eggs in a bowl of lukewarm water for 5 minutes, then dry them before use.
5. Pressing Down the Fruit : Ensures the pineapple and cherries stay vibrant when the cake is flipped, rather than being overly coated in caramel.
6. For a Glossy Finish : Brush the cake with warm corn syrup or slightly thinned apricot jam after unmolding for an extra shine.