Pineapple Upside Down Cake
This from-scratch Pineapple Upside Down Cake features golden caramelized pineapple rings and maraschino cherries atop a moist, tender vanilla cake. Made with real butter and a rich brown sugar caramel glaze, this showstopper dessert comes together in about an hour and looks far more impressive than the effort required — especially when you flip it over to reveal that gorgeous, glossy topping.
Equipment
- 10-inch cast iron skillet Traditional choice; or use a 10-inch round cake pan
- Round cake pan 10-inch; use if not using cast iron skillet
- Medium mixing bowl For dry ingredients
- Large mixing bowl For wet ingredients and cake batter
- Electric hand mixer or stand mixer For creaming butter and sugar
- Measuring cups and spoons
- Rubber spatula For spreading batter and scraping bowl
- Wire cooling rack
- Large serving plate Must be larger than pan for flipping
Ingredients
For the Topping
- 1/2 cup unsalted butter 113g, for the topping
- 1 cup light brown sugar 200g, packed
- 20 oz canned pineapple rings in juice 1 can (567g); drained, reserve ¼ cup juice
- 10 maraschino cherries up to 12; use halves to fill gaps
For the Cake
- 1 1/2 cups all-purpose flour 190g
- 1 1/2 tsp baking powder
- 1/4 tsp salt
- 1/2 cup unsalted butter 113g, softened to room temperature
- 3/4 cup granulated sugar 150g
- 2 large eggs room temperature
- 1 tsp vanilla extract pure vanilla recommended
- 1/2 cup whole milk 120ml, room temperature
- 1/4 cup reserved pineapple juice 60ml, from the drained can
Instructions
- Preheat your oven to 350°F (175°C). If using a regular cake pan, line the bottom with parchment paper; if using a cast iron skillet, place it on the stovetop over medium heat.
- Melt ½ cup butter in the skillet (or saucepan) over medium heat, add the brown sugar, and stir constantly for 2–3 minutes until the mixture bubbles and becomes a smooth, thick caramel. If using a cake pan, pour the caramel in and tilt to coat evenly; let cool 5 minutes.
- Pat the drained pineapple rings dry, then arrange one ring in the center of the pan and the remaining rings around it; place a maraschino cherry in the center of each ring and press everything gently into the caramel.
- In a medium bowl, whisk together the flour, baking powder, and salt for at least 30 seconds until evenly combined; set aside.
- Beat the softened butter with an electric mixer on medium speed for 1–2 minutes, then gradually add the granulated sugar and beat for 3–4 minutes until the mixture is pale, light, and fluffy.
- Add the eggs one at a time, beating well after each addition, then mix in the vanilla extract and scrape down the sides of the bowl.
- Mix the milk and reserved pineapple juice together, then alternate adding the flour mixture and the milk mixture to the butter mixture in three and two additions respectively, mixing on low just until no flour streaks remain — do not overmix.
- Pour the batter over the pineapple, spread evenly to the edges, tap the pan 2–3 times to release air bubbles, and bake on the middle rack for 45–50 minutes until a toothpick inserted in the center comes out with just a few moist crumbs.
- Let the cake cool in the pan for exactly 10 minutes, run a thin knife around the edges, then place a large serving plate over the pan and quickly flip them together; let sit 1–2 minutes before lifting the pan away.
Notes
- Use room temperature butter, eggs, and milk for the best batter — cold ingredients can lead to a denser cake.
- Pat the pineapple rings thoroughly dry before arranging; excess moisture prevents proper caramelization.
- Watch the caramel closely — brown sugar can burn quickly, so don't walk away during this step.
- The 10-minute cooling window before flipping is critical: too short and the topping slides, too long and it sticks. Set a timer.
- If the caramel hardens before you flip, place the pan in a 250°F oven for 3–4 minutes to soften it again.
- This cake tastes even better the next day as the flavors meld; make it up to 24 hours ahead and store covered at room temperature.
- Store leftovers covered at room temperature for up to 2 days, or refrigerated (wrapped tightly) for up to 5 days. Reheat slices in the microwave for 15–20 seconds.
- Freeze individual slices wrapped in plastic wrap then foil for up to 3 months.
- For a rum variation, stir 2 tablespoons dark rum into the caramel topping and 1 tablespoon into the batter.
- Cast iron is ideal for even caramelization, but a standard 10-inch round cake pan with parchment works perfectly well.
Nutrition
Serving: 1SliceCalories: 385kcalCarbohydrates: 58gProtein: 4gFat: 16gSaturated Fat: 10gPolyunsaturated Fat: 1gMonounsaturated Fat: 4gCholesterol: 75mgSodium: 180mgPotassium: 120mgFiber: 1gSugar: 42gVitamin A: 10IUVitamin C: 8mgCalcium: 6mgIron: 8mg
Tried this recipe?Let us know how it was!