Classic Pineapple Upside-Down Cake with Caramelized Fruit

Why You’ll Love This Recipe

• Classic, nostalgic flavor: buttery vanilla cake, caramelized pineapple, and cherries in every bite.
• Showstopping presentation with almost no decorating work—the fruit bakes into a glossy topping.
• Moist, tender crumb that stays soft for days thanks to sour cream and pineapple juice.
• Perfect for gatherings: can be served slightly warm or at room temperature and travels well.

Grocery List

• Produce: 1 can pineapple rings in juice, maraschino cherries
• Dairy: Unsalted butter, whole milk, sour cream (or plain yogurt), eggs
• Pantry: All-purpose flour, granulated sugar, light brown sugar, baking powder, salt, ground cinnamon, vanilla extract, nonstick spray or extra butter for greasing

Full Ingredients

For the Pineapple-Cherry Topping

• 4 tbsp (57 g) unsalted butter, melted, plus a little extra to grease the pan
• 2/3 cup (135 g) packed light brown sugar
• 1 can (20 oz / 567 g) pineapple rings in juice, drained, well patted dry
• 10–12 maraschino cherries, drained and patted dry
• 2–3 tbsp reserved pineapple juice (optional, for brushing the fruit after baking)

For the Buttery Vanilla Cake

• 1 1/2 cups (190 g) all-purpose flour, spooned and leveled
• 1 1/2 tsp baking powder
• 1/2 tsp fine salt
• 1/4 tsp ground cinnamon (optional, but delicious with pineapple)
• 1/2 cup (113 g) unsalted butter, softened to room temperature
• 3/4 cup (150 g) granulated sugar
• 1/4 cup (50 g) packed light brown sugar
• 2 large eggs, at room temperature
• 1 1/2 tsp pure vanilla extract
• 1/2 cup (120 ml) whole milk, at room temperature
• 1/4 cup (60 g) sour cream or plain full-fat yogurt, at room temperature
• 2 tbsp (30 ml) reserved pineapple juice (from the can)

Step-by-Step Instructions

Step 1: Prep the pan and preheat the oven

Preheat your oven to 350°F (175°C). Position a rack in the center of the oven.

Grease a 9-inch round cake pan (at least 2 inches deep) generously with butter or nonstick spray. For extra insurance against sticking, you can also line the bottom with a round of parchment paper and lightly grease the parchment as well.

Step 2: Make the caramel base and arrange the fruit

In a small bowl, stir together the 4 tbsp melted butter and 2/3 cup light brown sugar until you have a thick, sandy paste. Spread this mixture evenly over the bottom of the prepared pan, pressing it into the edges and corners so every bit of the base is covered.

Arrange the pineapple rings on top of the sugar mixture. Start with one ring in the center, then arrange more rings in a circle around it. Nestle a maraschino cherry into the center of each pineapple ring. If you have extra cherries, tuck them into any gaps between the rings for more color and sweetness. Set the pan aside while you make the cake batter.

Step 3: Whisk the dry ingredients

In a medium mixing bowl, whisk together the flour, baking powder, salt, and cinnamon (if using) until well combined and lump-free. This step helps the leavening and seasoning distribute evenly through the batter so the cake bakes up with a consistent texture. Set the dry mixture aside.

Step 4: Cream the butter and sugar, then add eggs and vanilla

In a large mixing bowl (or the bowl of a stand mixer fitted with the paddle attachment), add the 1/2 cup softened butter, 3/4 cup granulated sugar, and 1/4 cup brown sugar. Beat on medium speed for 2–3 minutes, scraping down the bowl as needed, until the mixture is light, fluffy, and slightly paler in color.

Add the eggs one at a time, beating well after each addition so the mixture becomes creamy and smooth. If it looks slightly curdled at this stage, that is okay—it will smooth out once the dry and wet ingredients are added. Beat in the vanilla extract.

Step 5: Combine the wet ingredients and bring the batter together

In a small bowl or measuring jug, whisk together the milk, sour cream (or yogurt), and pineapple juice until smooth. This mixture adds moisture, richness, and pineapple flavor to the cake.

With the mixer on low speed, add the dry ingredients to the creamed mixture in two additions, alternating with the milk mixture. So: add half the dry ingredients, mix gently; add all of the milk mixture, mix just until mostly combined; then add the remaining dry ingredients and mix until the batter is smooth and no dry flour remains. Avoid overmixing—stop as soon as everything is incorporated to keep the cake tender.

Step 6: Assemble and bake the cake

Carefully spoon the batter over the arranged pineapple and cherries in the pan. Use a spatula or the back of a spoon to gently spread it to the edges, taking care not to move the fruit underneath. The batter will be fairly thick; this is perfect for suspending the topping in place as it bakes.

Place the pan on the center rack and bake for 35–40 minutes, or until the top is golden brown and a toothpick or cake tester inserted into the center (not down into the fruit) comes out clean or with a few moist crumbs. If the cake is browning too quickly, you can loosely tent it with foil for the final few minutes of baking.

Step 7: Cool slightly, flip, and serve

Remove the cake from the oven and place it on a wire rack. Let it cool in the pan for 10–15 minutes. This short resting time allows the caramel to thicken slightly while still being fluid enough to release from the pan.

Run a thin knife around the edge of the cake to loosen any bits. Place a large serving plate or cake stand upside down over the pan. Using oven mitts, firmly grasp both pan and plate and quickly flip them together. Gently lift off the pan; the cake should slide out, revealing glossy pineapple rings and bright red cherries on top.

If desired, brush the warm fruit lightly with a spoonful or two of reserved pineapple juice for an extra sheen and moisture. Let the cake cool until just warm or to room temperature before slicing. Serve as is, or with softly whipped cream or vanilla ice cream.

Pro Tips

• Dry the fruit well: Patting the pineapple and cherries very dry helps the caramel cling and prevents a soggy topping.
• Use a deep pan: A 9-inch pan that is at least 2 inches deep is important to prevent overflow as the cake rises and the caramel bubbles.
• Do not skip the cooling time: Flipping too soon can make the topping run off; waiting too long can cause it to stick. Aim for 10–15 minutes.
• Room-temperature ingredients: Butter, eggs, milk, and sour cream should be at room temp so the batter emulsifies smoothly and bakes evenly.
• Check for doneness in the cake, not the fruit: Insert the tester into the cake portion near the center, not all the way to the bottom where the caramel is.

Variations

• Rum-infused: Replace 1–2 tbsp of the milk with dark or spiced rum, and brush a little rum over the fruit after baking for a gentle warmth and depth.
• Tropical twist: Add 1/4 cup finely chopped toasted coconut to the batter and sprinkle a little more coconut over the fruit right after flipping.
• Skillet version: Prepare the caramel directly in a 9- or 10-inch oven-safe cast-iron skillet, arrange the fruit, pour the batter on top, and bake as directed.

Storage & Make-Ahead

Once completely cool, cover the pineapple upside-down cake tightly with plastic wrap or transfer slices to an airtight container. Store at room temperature for up to 2 days, or in the refrigerator for up to 4 days. For the best texture, bring refrigerated cake back to room temperature or warm individual slices in the microwave for 10–15 seconds before serving.

You can bake the cake up to a day ahead of serving. Flip it out of the pan while still slightly warm, let it cool completely, then cover. The flavors often deepen by the next day, and the cake stays wonderfully moist.

Nutrition (per serving)

Approximate values for 1 slice (1/10 of the cake): about 430 calories, 20 g fat (12 g saturated), 60 g carbohydrates (about 38 g sugars), 4 g protein, and 1 g fiber. These numbers are estimates and will vary based on exact ingredients and portion sizes.