Pineapple Upside-Down Cake

Get ready for the most impressive dessert that’s actually a breeze to make! This retro-fabulous pineapple upside-down cake brings major wow factor with its glistening caramelized fruit top and incredibly moist vanilla cake base.

Those gorgeous rings of pineapple, each crowned with a cherry jewel, create an absolutely stunning pattern that’ll have everyone reaching for their phones to snap a pic before diving in. But the real magic happens when you take that first bite – the brown sugar caramel mingles with juicy pineapple and tender cake for a flavor combination that’s pure nostalgia meets modern-day delicious.

Ingredients

For the topping:

• Cooking spray
• 4 tablespoons unsalted butter
• 1/2 cup packed light brown sugar
• 1 (8-ounce) can pineapple rings in pineapple juice
• 8 to 10 maraschino cherries

For the cake:

• 1 1/2 cups all-purpose flour
• 1 teaspoon baking powder
• 1/4 teaspoon salt
• 1 cup granulated sugar
• 8 tablespoons (1 stick) unsalted butter, at room temperature
• 2 large eggs

Steps

1. Position a rack in the middle of the oven and preheat to 350°F (175°C). Thoroughly coat a 9-inch round cake pan with cooking spray, making sure to get the sides.
2. Create the caramel topping: In a small saucepan over medium heat, melt 4 tablespoons butter with 1/2 cup brown sugar, stirring frequently. You’ll know it’s ready when the mixture is actively bubbling and turns slightly darker brown (3-4 minutes).
3. Working quickly while the caramel is hot, pour it into your prepared pan. Use a spatula to spread it evenly – it will start to set as it cools.
4. Drain the pineapple rings, reserving exactly 1/2 cup of the juice for the cake batter. Create a beautiful pattern by placing one ring in the center, then arrange 6-7 rings around it. Place a maraschino cherry in each ring’s center.
5. Mix your dry ingredients: Whisk together 1 1/2 cups flour, 1 teaspoon baking powder, and 1/4 teaspoon salt in a medium bowl until well combined.
6. For the cake batter, beat 1 cup sugar with room temperature butter using an electric mixer on medium speed for 5 minutes until light and fluffy. The mixture should be pale yellow and noticeably increased in volume. Add eggs one at a time, beating for 30 seconds after each.
7. Now comes the crucial alternating method: With mixer on low, add flour mixture in 3 parts, alternating with 2 parts pineapple juice. Begin and end with flour (flour-juice-flour-juice-flour), mixing each addition for 30 seconds. This method prevents the batter from curdling.
8. Carefully spoon the thick batter over your pineapple arrangement. Use an offset spatula to gently spread it evenly without disturbing the fruit. Tap the pan 3-4 times on the counter to remove air bubbles.
9. Bake for 45-50 minutes until deeply golden brown. A toothpick inserted in the center should come out clean, and the internal temperature should reach 200°F (93°C). Cool for exactly 10 minutes – no longer, or the caramel will stick!
10. For the flip: Place your serving plate over the pan, then quickly but confidently invert everything in one smooth motion. Wait 30 seconds, then slowly lift the pan away. Serve warm or at room temperature.

Smart Swaps

• Replace 1/2 cup butter with 1/2 cup unsweetened applesauce for a lighter version
• Use fresh pineapple rings (about 1 medium pineapple) instead of canned
• Swap maraschino cherries for fresh dark sweet cherries when in season

Make It Diabetes-Friendly

• Use a 1:1 sugar substitute like monk fruit sweetener (reduces carbs by 15g per serving)
• Replace 1/2 cup of all-purpose flour with 1/2 cup almond flour
• Serve 3-inch portions paired with protein to slow sugar absorption
• Use fresh pineapple in thinner slices to reduce natural sugars while maintaining flavor

Pro Tips

• Room temperature eggs create a more even, tender crumb
• Don’t skip the pan-tapping step – it prevents air pockets
• If caramel hardens while spreading, warm the pan slightly over low heat
• Use a sharp knife dipped in hot water to get clean slices