Pineapple Upside-Down Cake with Caramelized Fruit

Quick Recipe Version (TL;DR)

• Yield: 10 servings
• Prep Time: 25 minutes
• Cook Time: 40 minutes
• Total Time: 1 hour 20 minutes

Quick Ingredients

• 4 tbsp (57 g) unsalted butter + 1/2 cup (100 g) packed light brown sugar (topping)
• 1 can (20 oz/567 g) pineapple rings in juice, well drained and patted dry
• 10–12 maraschino cherries, drained and patted dry
• 1 1/2 cups (195 g) all-purpose flour
• 3/4 cup (150 g) granulated sugar
• 1 1/2 tsp baking powder + 1/2 tsp kosher salt
• 2 large eggs, room temp
• 1/2 cup (113 g) unsalted butter, melted and cooled
• 1/2 cup (120 ml) whole milk, room temp
• 1/4 cup (60 ml) pineapple juice (from can)
• 1/4 cup (60 g) sour cream
• 2 tsp pure vanilla extract

Do This

• 1. Heat oven to 350°F (177°C). Butter a 9-inch round cake pan (2 inches deep).
• 2. Simmer 4 tbsp butter + 1/2 cup brown sugar until bubbly; pour into pan.
• 3. Arrange pineapple rings over caramel; tuck cherries in centers and gaps.
• 4. Whisk dry: flour, sugar, baking powder, salt. In another bowl whisk eggs, melted butter, milk, pineapple juice, sour cream, vanilla.
• 5. Combine wet into dry just until smooth. Spread over fruit; level.
• 6. Bake 38–45 minutes until golden and a tester has a few moist crumbs.
• 7. Cool 10 minutes, loosen edges, invert onto a platter; brush any pan syrup over top. Slice warm.

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Why You’ll Love This Recipe

• Caramel-kissed pineapple and cherries create a glossy, irresistible top that’s the star of the show.
• One bowl batter with pantry staples—no mixer required.
• Flip it warm so the buttery brown sugar syrup soaks into the tender vanilla crumb.
• Classic nostalgia with sunny, island-inspired flavor in every bite.

Grocery List

• Produce: None required (canned pineapple rings and maraschino cherries)
• Dairy: Unsalted butter, whole milk, sour cream
• Pantry: All-purpose flour, granulated sugar, light brown sugar, baking powder, kosher salt, pure vanilla extract, canned pineapple rings in juice, maraschino cherries

Full Ingredients

For the Caramel Topping

• 4 tbsp (57 g) unsalted butter
• 1/2 cup (100 g) packed light brown sugar
• 1 can (20 oz/567 g) pineapple rings in juice, drained very well and patted dry (you’ll use 7–8 rings)
• 10–12 maraschino cherries, drained and patted dry

For the Vanilla Cake

• 1 1/2 cups (195 g) all-purpose flour
• 3/4 cup (150 g) granulated sugar
• 1 1/2 tsp baking powder
• 1/2 tsp kosher salt
• 2 large eggs, at room temperature
• 1/2 cup (113 g) unsalted butter, melted and slightly cooled
• 1/2 cup (120 ml) whole milk, at room temperature
• 1/4 cup (60 ml) pineapple juice, reserved from the can
• 1/4 cup (60 g) sour cream
• 2 tsp pure vanilla extract

To Serve (optional)

• Lightly sweetened whipped cream or vanilla ice cream
• Toasted coconut flakes

Step-by-Step Instructions

Step 1: Prep the pan and oven

Heat the oven to 350°F (177°C). Generously butter the sides of a 9-inch round cake pan (2 inches deep). Do not line with parchment; the fruit needs direct contact with the caramel to release cleanly. Set a heatproof platter slightly larger than the pan aside for inverting later.

Step 2: Make the brown sugar–butter caramel

In a small saucepan over medium heat, melt 4 tbsp (57 g) butter with 1/2 cup (100 g) packed light brown sugar, stirring until the mixture is smooth and just bubbling, 1–2 minutes. Immediately pour the hot caramel into the prepared cake pan and tilt to coat the bottom evenly.

Step 3: Arrange pineapple and cherries

Pat the pineapple rings and cherries very dry so they don’t dilute the caramel. Lay one ring in the center of the pan and arrange 6–7 rings around it. Nestle a cherry in each ring’s center and in any open spaces. Press gently so the fruit sits flat in the caramel.

Step 4: Mix the dry ingredients

In a large bowl, whisk together the flour, granulated sugar, baking powder, and salt.

Step 5: Whisk the wet ingredients and make the batter

In a medium bowl, whisk the eggs, melted butter, milk, pineapple juice, sour cream, and vanilla until smooth. Pour the wet mixture into the dry ingredients and whisk just until combined and no dry streaks remain. The batter should be thick but pourable—avoid overmixing for a tender crumb.

Step 6: Bake

Scrape the batter over the arranged fruit and spread evenly to the edges. Tap the pan firmly on the counter to release air bubbles. Bake on the center rack for 38–45 minutes until the top is deep golden and a toothpick inserted into the cake (not the fruit) comes out with a few moist crumbs. An instant-read thermometer inserted in the center should read about 200°F (93°C).

Step 7: Cool briefly and flip

Cool the cake in the pan for 10 minutes on a rack. Run a thin knife around the edge to loosen. Place your serving platter over the pan and, with oven mitts, invert in one confident motion. Lift off the pan; if any fruit sticks, gently place it back on the cake. Spoon or brush any pan syrup over the top. Let rest 10–15 minutes before slicing. Serve warm with whipped cream or a scoop of vanilla ice cream.

Pro Tips

• Dry the fruit well—excess moisture can prevent caramelization and make the top watery.
• If the cake is browning too quickly, tent loosely with foil for the last 10 minutes.
• Weighing flour (195 g) helps avoid a dense cake. If using cups, fluff, spoon, and level.
• Flip after exactly 10 minutes of cooling; too soon and it may break, too late and the caramel can set.
• For ultra-shiny fruit, warm 1 tbsp pineapple juice with 1 tsp sugar and brush on before serving.

Variations

• Coconut-Lime: Replace 1/4 cup (30 g) flour with unsweetened shredded coconut, add 1 tsp lime zest to the batter, and finish with a squeeze of lime.
• Rum Soaked: Brush the warm inverted cake with 1–2 tbsp dark rum for a grown-up, tropical note.
• Fresh Pineapple: Use 1/2-inch-thick fresh rings lightly sautéed in 1 tbsp butter for 2–3 minutes per side to concentrate flavor before arranging in the pan.

Storage & Make-Ahead

Store covered at room temperature for up to 1 day or in the refrigerator for up to 4 days. Rewarm slices in a 300°F (150°C) oven for 8–10 minutes or microwave briefly until the caramel softens. To freeze, wrap individual slices tightly and freeze for up to 2 months; thaw overnight in the fridge and rewarm. You can drain and pat the pineapple and cherries up to 1 day ahead and refrigerate; assemble and bake just before serving for best texture.

Nutrition (per serving)

Approximate for 1 of 10 servings: 360 calories; 16 g fat; 48 g carbohydrates; 27 g sugars; 5 g protein; 1 g fiber; 220 mg sodium. Values are estimates.