This timeless pineapple upside-down cake recipe is a nostalgic dessert that’s as beautiful as it is delicious. Featuring juicy pineapple rings, vibrant maraschino cherries, and a rich vanilla cake infused with pineapple juice, this homemade upside-down cake is the perfect dessert for any occasion. Whether you’re baking for a holiday, a birthday, or just because, this retro dessert never goes out of style.

Let’s dive into how you can recreate this showstopping treat from scratch with pantry staples and a few expert tips to make sure it turns out bakery-quality every single time.

Why You’ll Love This Pineapple Upside-Down Cake

This moist pineapple cake is packed with tropical flavor and buttery goodness. The caramelized brown sugar topping blends beautifully with the sweet pineapple and cherries, creating a stunning glossy top when flipped. The fluffy, tender vanilla sponge soaks up the fruit juices and is dotted with chopped pineapple bits for an extra punch of tropical flavor.

Even better? We use the reserved pineapple juice from the can in the batter itself—maximizing flavor and minimizing waste!

Ingredients for the Ultimate Pineapple Upside-Down Cake

Here’s everything you’ll need to create this tropical classic from scratch:

For the Fruit Topping:

565g (20 oz) canned pineapple slices in juice (avoid syrup-packed versions)

12 to 18 maraschino cherries (adjust to taste)

60g (4 tbsp) unsalted butter, melted

½ cup brown sugar

For the Vanilla Pineapple Cake:

1½ cups all-purpose flour

1 tsp baking powder

¼ tsp baking soda (can substitute with 1 extra tsp of baking powder)

¼ tsp salt

⅓ cup whole or low-fat milk

¼ cup reserved pineapple juice from the canned fruit

¼ cup full-fat sour cream (plain Greek yogurt works too)

1 tsp pure vanilla extract

115g (1 stick) unsalted butter, softened to about 18°C/64°F

¾ cup white sugar

2 large eggs, room temperature

Any leftover pineapple from the can, finely chopped

How to Make Pineapple Upside-Down Cake

1. Get Prepped

Preheat your oven to 180°C (350°F) or 160°C if using a fan-forced oven. You’ll need a 23cm (9-inch) round cake pan with sides at least 5cm (2 inches) high. Avoid using springform pans as the sugary topping may leak.

2. Prepare the Fruit Topping

Start by laying your pineapple slices and maraschino cherries on a paper towel-lined tray. Pat them gently to remove excess moisture, which helps them caramelize without steaming.

Pour the melted butter into your cake pan and use a pastry brush to coat the bottom and sides. Sprinkle brown sugar evenly across the bottom.

Place one pineapple slice in the center, then surround it with halved or whole pineapple rings, arranging them however you prefer. Decorate the centers of each pineapple ring with maraschino cherries. Press all the fruit down firmly into the sugar mixture so they’re in full contact with the bottom of the pan—this helps give them their bright, glossy finish once baked and flipped.

3. Make the Cake Batter

Mix the Dry Ingredients

In a bowl, whisk together flour, baking powder, baking soda, and salt. Set aside.

Combine the Wet Ingredients

In another bowl, whisk together milk, pineapple juice, sour cream, and vanilla extract until smooth.

Cream the Butter and Sugar

In a third bowl, beat the softened butter and white sugar using a handheld or stand mixer on medium-high speed for about 2 minutes until pale and fluffy.

Add Eggs

Add one egg at a time, beating for about 20 seconds after each addition until fully incorporated.

Combine Wet and Dry

Using a rubber spatula, alternate between adding the flour mixture and the milk mixture:

Add ⅓ of the dry mix and stir

Add ½ of the wet mixture and stir

Repeat until all ingredients are combined

Fold in the chopped leftover pineapple for extra bursts of tropical sweetness throughout the cake.

4. Assemble and Bake

Carefully pour the batter over your arranged fruit and gently spread it to the edges, smoothing out the top. Bake in the center of your oven for 30 minutes. Then loosely cover with foil and bake for an additional 15 minutes or until a skewer or toothpick inserted in the center comes out clean.

5. Cool and Flip

Let the cake rest in the pan for 20 minutes. Then run a butter knife along the edge of the pan to loosen it. Place your serving platter over the top and carefully invert the pan. Gently tap or shake to release the cake.

Let it cool completely before slicing.

Tips for Success

Use juice-packed pineapple: Skip syrup-packed versions, which are overly sweet and lack the zesty juice needed for the batter.

Dry the fruit thoroughly: Wet pineapple or cherries can ruin the caramelization and cause soggy spots in your topping.

Room temperature ingredients are key: Softened butter and room-temp eggs ensure a smooth batter and even texture.

Don’t overmix the batter: Gently folding helps avoid dense cake.

Cool before flipping: Trying to flip it too early could cause the cake to break apart.

Optional Glaze for Extra Shine

Want your upside-down cake to look like it belongs in a bakery window? After flipping, brush the fruit topping with a bit of warm corn syrup or slightly thinned apricot jam for a glossy finish.

Storing Leftovers

Store your pineapple upside-down cake in the refrigerator for up to 5 days. Make sure it’s covered well with plastic wrap or in an airtight container. For best results, bring to room temperature before serving to allow the flavors to shine.

Make-Ahead Tip

You can bake the cake a day in advance and store it covered at room temperature. Flip just before serving to ensure it looks fresh and vibrant.

FAQs

Can I use fresh pineapple instead of canned?
Yes! Just be sure to slice it evenly and simmer it briefly in water and sugar to soften it. However, you’ll miss out on the pineapple juice that’s used in the batter.

What if I don’t have sour cream?
You can substitute full-fat Greek yogurt, but sour cream gives a slightly richer texture.

Can I use butter substitutes like margarine?
It’s best to use real unsalted butter. Margarine contains more water and will affect the texture and flavor.

Why is my cake dense?
This could be due to overmixing the batter or using butter that was too warm. The ideal butter temperature is around 18°C/64°F.

Can I freeze this cake?
Yes! Wrap tightly in plastic and freeze for up to 2 months. Thaw at room temperature before serving.

Pineapple Upside-Down Cake Recipe

This classic pineapple upside-down cake is soft, golden, and rich with buttery caramel flavor. It’s topped with sweet pineapple rings and cherries baked into a brown sugar glaze perfect for any gathering or Sunday dessert.

Prep Time: 20 minutes
Cook Time: 45 minutes
Cooling Time: 20 minutes
Total Time: 1 hour 25 minutes
Servings: 12 slices

Ingredients

For the Topping:
1 can (565g / 20 oz) pineapple slices in juice
12–18 maraschino cherries
60g (4 tbsp) unsalted butter, melted
½ cup brown sugar

For the Vanilla Cake:
1½ cups all-purpose flour
1 tsp baking powder
¼ tsp baking soda (or use 1 extra tsp baking powder)
¼ tsp salt
⅓ cup milk (whole or low-fat)
¼ cup reserved pineapple juice
¼ cup sour cream (or Greek yogurt)
1 tsp vanilla extract
115g (1 stick) unsalted butter, softened
¾ cup white sugar
2 large eggs
Chopped leftover pineapple (from the can)

Instructions

Preheat oven to 180°C (350°F) or 160°C fan-forced. Grease a 23cm (9-inch) round cake pan. Avoid using a springform pan as the topping may leak during baking.

Pour melted butter into the bottom of the pan and sprinkle brown sugar evenly on top. Pat the pineapple slices and cherries dry with paper towels. Arrange pineapple rings in the pan and place a cherry in the center of each ring.

In one bowl, whisk together the flour, baking powder, baking soda, and salt. In a separate bowl, whisk together the milk, pineapple juice, sour cream, and vanilla extract.

In a large mixing bowl, cream the softened butter and sugar using an electric mixer until light and fluffy. Add eggs one at a time, beating well after each addition. Add the flour mixture and milk mixture alternately in batches, beginning and ending with the dry ingredients. Fold in chopped pineapple.

Pour the batter over the arranged fruit in the pan and smooth the surface. Bake for 30 minutes, then loosely cover with foil and bake for another 15 minutes, or until a toothpick inserted into the center comes out clean.

Cool the cake in the pan for 20 minutes. Run a knife around the edges, place a serving plate over the top, and carefully invert to release the cake.

Storage Tips

Refrigerate leftovers in an airtight container for up to 5 days. To freeze, wrap the cake tightly and store for up to 2 months. Thaw at room temperature before serving.

Nutrition Information (per slice, approx. 12 servings)
Calories: 280–320 kcal
Carbohydrates: 40–45 g
Protein: 3–4 g
Fat: 12–14 g
Saturated Fat: 7–8 g
Cholesterol: 60–70 mg
Sodium: 120–150 mg
Fiber: 1 g
Sugar: 25–30 g

Nutrition may vary depending on specific brands and quantities used.