Pineapple Upside Down Cake

The old school dessert deserves the spotlight!

Arman Liew
May 14, 2026

Some recipes just feel like a memory, even the first time you make them. This is one of those.

Pineapple upside down cake is one of those old-school classics that never actually went out of style- it just got forgotten for a while (like my honey cake). And honestly? It deserves its moment back.

There’s no fancy technique here, no special equipment, and nothing that requires you to be a confident baker. Just a pan, a bowl, and about an hour until you’re flipping the most beautiful, caramelized, retro-gorgeous cake onto a plate and feeling genuinely proud of yourself.

Let’s talk about that topping, though- because that’s really the whole point. The butter and brown sugar bubble together underneath the pineapple as it bakes, slowly turning into this deeply golden, sticky caramel that soaks into the edges of every slice. The cherries are non-negotiable. Don’t @ me.

The cake itself is tender and just rich enough- oil and sour cream keep it moist for days, and a splash of pineapple juice goes straight into the batter so the flavor isn’t just sitting on top.

Cooking Science

The magic here is all in the timing and temperature. The brown sugar and butter melt into a slow caramel beneath the fruit while the batter bakes above it- the two layers essentially fuse together at the edges, which is what gives you those gorgeous, lacquered slices.

Baking low and steady at 350°F lets the center cook through before the caramel has any chance of burning. And that 10-minute rest before inverting? Non-negotiable- it lets the caramel firm up just enough to release cleanly instead of dripping down the sides of the pan.

Recipe

• 1 1/2 cups all-purpose flour
• 1 1/2 teaspoons baking powder
• 1/4 teaspoon salt
• 1/2 cup oil
• 1/3 cup milk, room temperature
• 1/4 cup pineapple juice
• 1/3 cup sour cream or Greek yogurt
• 1 teaspoon vanilla extract
• 3/4 cup sugar
• 2 large eggs, room temperature

For the topping:

• 1/4 cup butter, melted
• 1/2 cup light brown sugar
• 20 ounces canned pineapple in its own juices
• 1/4 cup maraschino cherries

1. Preheat the oven to 180°C/350°F.

2. To make the topping, pour the melted butter into a 9-inch cake pan and sprinkle the brown sugar evenly over the top. Arrange the pineapple slices over the sugar and place a cherry in the center of each slice. Chop any leftover pineapple into small pieces and scatter them around the pan.

3. In a medium bowl, whisk together the flour, baking powder, and salt. In a separate large bowl, whisk together the oil, milk, pineapple juice, sour cream, vanilla extract, and sugar until smooth. Add the eggs and whisk until fully combined.

4. Gradually fold the dry ingredients into the wet mixture, stirring until just combined.

5. Pour the batter over the pineapple layer and smooth the top.

6. Bake for 40–45 minutes, or until a toothpick inserted into the center comes out clean.

7. Let the cake cool for 10 minutes, then run a knife around the edges and carefully invert onto a serving plate.

How to flip an upside down cake

Grab your oven mitts (the pan will be hot!) and a large serving platter or dinner plate before flipping the cake right side up:

1. Run a knife along the edges of the cake in the pan.
2. Turn your serving platter upside down and place it on top of the baked cake still in the cake pan.
3. Using oven mitts, grip both the serving platter and the cake pan with both of your hands.
4. Carefully and quickly flip everything. The platter should be on the bottom and the cake pan on top of the platter.
5. Gently tap the bottom of the cake pan, then slide it up and off the cake.

Arman ‘s recipe tips

• Dry the pineapple slices with paper towels before layering them in the cake pan. There are two reasons for this: (1) You’ll avoid excess moisture in the cake, and (2) the dried pineapple is better at absorbing the caramelized brown sugar.

• Chop up any leftover pineapple slices and scatter them around the cake pan before pouring the batter on top.

• Don’t add the eggs all at once. Beating them into the wet mixture separately will incorporate more air into the batter, leaving you with a fluffier cake.

• Don’t overmix the batter! Only stir the dry mixture into the wet until the two are just incorporated together and no dry flour streaks remain.

• Use a bundt pan. For a pineapple upside down bundt cake, simply swap out the standard cake pan for a bundt pan instead.