Pineapple upside down cake is a nostalgic favorite that has been loved for generations.

It’s the kind of dessert that feels both special and familiar, with its caramelized topping of golden pineapples and bright cherries sitting over a soft, buttery cake.

This cake became popular in the early 1900s, right around the time canned pineapple became widely available.

By the 1950s, it was a household staple, often served at family gatherings, church socials, and potlucks.

The beauty of this cake isn’t just in its flavor—it’s in the magic that happens when you flip it over after baking, revealing a gorgeous, glossy fruit topping.

It’s simple enough to make on a weekday but impressive enough to serve on special occasions.

If you’ve never made one before, you’re in for a treat. It’s rich, moist, and perfectly balanced between the sweetness of the caramelized brown sugar and the slight tang of pineapple.

The best part? You don’t need any fancy ingredients or complicated techniques. Just a handful of pantry staples, a little patience, and a love for classic desserts.

Pineapple Upside Down Cake Recipe

Ingredients

Topping

• 6 tablespoons softened butter
• 1 cup packed brown sugar
• ¼ cup fresh pineapple juice (from canned or freshly squeezed)
• 1-2 tablespoons apple cider vinegar
• 8 pineapple rings (canned in natural juice or fresh)
• 12-15 pecan halves (or walnuts for variation)
• 8 fresh or maraschino cherries

Cake

• 7 ounces butter (or coconut oil for vegan option)
• 1¼ cups granulated sugar
• 3 eggs (or flaxseed eggs for vegan: 1 tbsp ground flax + 3 tbsp water per egg)
• 2¼ cups all-purpose flour (or gluten-free flour blend for gluten-free option)
• ¾ cup thick yogurt (or dairy-free yogurt for vegan option)
• 1 teaspoon pure vanilla extract
• 1 teaspoon baking powder
• ½ teaspoon baking soda
• ¼ teaspoon salt

Instructions

Preparing The Topping

1. Let the pineapple slices and cherries dry on a paper towel to remove excess moisture.
2. In a large oven-safe skillet or round cake pan, melt the butter over low heat until it starts bubbling.
3. Stir in the brown sugar and cook for about 3 minutes until the mixture turns smooth.
4. Carefully mix in the pineapple juice and apple cider vinegar. Be cautious as the liquid may splatter if the mixture is too hot.
5. Remove from heat and arrange the pineapple slices in a decorative pattern. Place cherries in the center of each pineapple ring and pecans in the remaining gaps.

Making The Cake

1. Preheat your oven to 325°F (163°C).
2. In a large mixing bowl, beat the butter and sugar together until the texture becomes light and fluffy.
3. Add eggs one at a time, mixing well after each addition. Stir in the vanilla extract.
4. In a separate bowl, whisk together the flour, baking powder, baking soda, and salt.
5. Gradually add the dry ingredients to the butter mixture, alternating with the yogurt. Mix until just combined.
6. Gently spread the batter over the pineapple layer, smoothing the surface evenly with a spatula.
7. Bake for about 45-50 minutes or until a toothpick inserted in the center comes out clean.
8. Let the cake cool for about 5 minutes before carefully flipping it onto a serving plate.

Useful Tips For Pineapple Upside Down Cake

Getting a perfect pineapple upside down cake isn’t just about following the recipe—it’s about small details that make a big difference. Here’s what actually matters:

• Prevent a soggy cake: Too much liquid can ruin the texture. Drain the pineapple slices well and pat them dry before using. If using canned cherries, dry those too.
• Avoid a stuck cake: Grease your pan generously with butter or nonstick spray. A well-greased pan helps the cake release easily without breaking apart.
• Even caramelization: Melt the butter and brown sugar properly—cook it until it’s fully dissolved but not burned. This gives you a smooth, caramel-like topping instead of a grainy one.
• Cake texture matters: Don’t overmix the batter. Stir just until everything is combined, or the cake might turn out dense and tough.
• Flipping it correctly: Let the cake sit for about 5 minutes after baking, then run a knife around the edges and flip it onto a plate while it’s still warm. Waiting too long can make the topping stick to the pan.

How To Store Pineapple Upside Down Cake?

Keeping your cake fresh depends on how soon you plan to eat it. Here’s the best way to store it based on your needs:

Short-term storage (1-2 days):

• Leave the cake at room temperature, covered with plastic wrap or placed in an airtight container. Keep it in a cool spot, away from heat or sunlight.

Refrigeration (Up to 4 days):

• If you need to store it longer, refrigerate it. Cover the cake well to prevent it from drying out. Before serving, let it sit at room temperature for about 30 minutes so it’s soft and moist again.

Freezing (Up to 3 months):

• Wrap the cake tightly in plastic wrap, then in aluminum foil. When ready to eat, thaw it in the fridge overnight and bring it to room temperature before serving.

How Long Should You Leave A Pineapple Upside Down Cake Before Cutting?

Timing is important when it comes to slicing this cake.

• After baking, let it rest in the pan for 5 minutes—this allows the topping to set without sticking.
• Flip the cake onto a plate while it’s still warm, then wait about 15-20 minutes before cutting. This helps the cake firm up slightly so it doesn’t fall apart.

Cutting it too soon can make it too soft, while waiting too long may cause the topping to harden.

Should You Use Parchment Paper When Baking A Pineapple Upside Down Cake?

Parchment paper isn’t necessary, but it can help if you’re worried about sticking.

• If using parchment, cut a circle to fit the bottom of the pan and grease it well. This makes flipping even easier.
• However, a well-greased pan with melted butter and brown sugar usually works just fine, as the caramelized topping naturally releases the cake when flipped at the right time.

Does Turning A Pineapple Upside Down Help It Ripen?

No, flipping a whole pineapple upside down doesn’t actually speed up ripening. Pineapples stop ripening once they’re picked.

However, turning it upside down for a few hours before cutting can help redistribute the juices, making the flavor more even throughout the fruit.

But if your pineapple is underripe, no trick will make it sweeter—it’s best to choose one that already smells sweet and has a slight give when pressed.