This Next-Level Pineapple Upside-Down Cake is a sweet escape to the tropics, blending caramelized pineapple rings with a moist, buttery cake. The golden-brown crust gives way to a tender crumb, while the juicy fruit adds a burst of tangy freshness.
In just 20 minutes of prep and 35 minutes of baking, you’ll create a dessert that’s as stunning as it is delicious. Perfect for impressing guests or treating yourself, this cake is a harmonious balance of rich, sweet, and fruity flavors.
Every bite offers a delightful contrast of textures—crisp edges, soft cake, and succulent pineapple. The caramel glaze seeps into the cake, creating a luscious, gooey layer that’s impossible to resist.
Whether served warm or at room temperature, this cake is a crowd-pleaser that feels both nostalgic and elevated. With minimal effort and maximum reward, it’s the ultimate dessert to brighten any occasion.
Ingredients for Next-Level Pineapple Upside-Down Cake
- For the Caramel:
- ½ cup (4oz/115g) butter
- 1 ¼ cups (7½oz/213g) dark brown sugar
- 1 large can (20oz/567g) sliced pineapple in juice (reserve ½ cup juice for the cake)
- 10-13 maraschino cherries (stems removed)
- For the Cake:
- ½ cup (4oz/115g) butter, softened
- ½ cup (4oz/115g) granulated sugar
- ⅓ cup (2oz/57g) dark brown sugar
- 2 large eggs
- ½ cup (4floz/120ml) whole milk
- ½ cup (4floz/120ml) reserved pineapple juice
- 1 teaspoon almond extract (or vanilla extract as a substitute)
- 2 cups (10oz/284g) all-purpose flour
- 2 teaspoons baking powder
- ½ teaspoon salt
Step-by-Step Instructions
- Preheat the oven: Set your oven to 350°F (180°C). Generously butter a 9×13-inch (23x33cm) baking pan and set aside.
- Make the caramel: In a small saucepan over medium-low heat, combine ½ cup butter and 1 ¼ cups dark brown sugar. Simmer for 2-3 minutes until the sugar dissolves. Pour this mixture into the prepared baking pan.
- Arrange the pineapple and cherries: Drain the pineapple rings, reserving ½ cup of the juice for the cake. Arrange the rings in a single layer (4×3 or as many as fit) on top of the caramel. Place a maraschino cherry in the center of each ring.
- Prepare the cake batter: In a medium bowl, whisk together 2 cups flour, 2 teaspoons baking powder, and ½ teaspoon salt. Set aside.
- Cream the butter and sugars: In a large bowl, cream together ½ cup softened butter, ⅓ cup dark brown sugar, and ½ cup granulated sugar until light and fluffy.
- Add the eggs: Whisk in one egg at a time, ensuring each is fully incorporated before adding the next.
- Combine wet and dry ingredients: Gradually mix the dry ingredients into the butter-sugar mixture until it resembles breadcrumbs. Slowly stream in ½ cup milk and ½ cup reserved pineapple juice. Finally, add 1 teaspoon almond extract and mix until just combined. The batter should be light and fluffy.
- Assemble and bake: Carefully spread the batter over the pineapple layer in the pan. Bake for 35-40 minutes, or until a wooden skewer inserted into the center comes out clean.
- Cool and serve: Let the cake cool in the pan for 10 minutes, then invert it onto a serving tray. Serve warm or at room temperature. Store leftovers in an airtight container at room temperature for up to 2 days.
Perfect Pairings: Serving Suggestions
This Next-Level Pineapple Upside-Down Cake shines on its own, but you can elevate it further with a dollop of freshly whipped cream or a scoop of vanilla ice cream. For a tropical twist, try serving it with a drizzle of coconut cream or a sprinkle of toasted coconut flakes. Pair it with a cup of coffee or tea for a delightful afternoon treat.
Storage Secrets: Keeping It Fresh
This cake is best enjoyed the day it’s made, but if you have leftovers, store them in an airtight container at room temperature for up to 2 days. To maintain its moisture, place a piece of parchment paper over the cut edges. For longer storage, wrap individual slices tightly in plastic wrap and freeze for up to 1 month—thaw at room temperature before serving.
Time-Saving Tips for Busy Bakers
To streamline the process, measure and prep all your ingredients before starting. Use a stand mixer to cream the butter and sugars for a quicker, fluffier result. If you’re short on time, skip the pineapple juice step and use the juice straight from the can—it’s already perfectly sweet and tangy!
Recipe Variations to Mix It Up
Feel free to get creative with this recipe! Swap pineapple rings for fresh mango or peach slices for a fruity twist. Add a pinch of cinnamon or nutmeg to the batter for a warm, spiced flavor. For a nutty crunch, fold in ½ cup of chopped pecans or walnuts before baking. The possibilities are endless!
Equipment Essentials for Success
A 9×13-inch baking pan is ideal for this recipe, but a 10-inch cast-iron skillet works beautifully for a rustic presentation. Use a wooden skewer or toothpick to test for doneness—it should come out clean when the cake is ready. A sturdy spatula or offset knife will help spread the batter evenly over the pineapple layer.
Next-Level Pineapple Upside-Down Cake
Ingredients
For the Caramel:
- ½ cup butter 4oz/115g
- 1 ¼ cups dark brown sugar 7½oz/213g
- 1 large can sliced pineapple in juice 20oz/567g
- 10-13 maraschino cherries stems removed
For the Cake:
- ½ cup butter, softened 4oz/115g
- ½ cup granulated sugar 4oz/115g
- ⅓ cup dark brown sugar 2oz/57g
- 2 large eggs
- ½ cup whole milk 4floz/120ml
- ½ cup juice from the tinned pineapple 4floz/120ml
- 1 teaspoon almond extract
- 2 cups all-purpose flour 10oz/284g
- 2 teaspoons baking powder
- ½ teaspoon salt
Instructions
- Preheat the oven to 350°F (180°C) and generously butter a 9×13-inch (23x33cm) baking pan. Set aside.
- In a small saucepan over medium-low heat, combine butter and brown sugar and simmer until the sugar is dissolved in about 2-3 minutes. Pour into the prepared baking pan.
- Drain the pineapple rings and reserve ½ cup (4floz/120ml) of juice. Arrange as many rings 4 x 3 or as you can fit in a single layer in the pan on top of the butter and brown sugar mixture.
- Place a maraschino cherry in the center of each pineapple ring.
- In a medium mixing bowl, combine the flour, baking powder and salt, mix well and set aside.
- In a large bowl cream together room temperature butter, dark brown sugar and granulated sugar until light and fluffy.
- To the butter-sugar mixture, whisk in the first egg and cream it until fully incorporated. Add in the second egg and cream it until fully incorporated, too.
- Then mix in the dry ingredients until it comes together and resembles bread crumbs.
- Slowly stream in milk followed by the reserved pineapple juice.
- At last, measure and pour in almond extract. Mix all until just combined and the batter is light and fluffy.
- Carefully spread the batter over the pineapples and then bake for 35-40 minutes, until a wooden skewer inserted into the center comes out clean.
- Let the cake cool for 10 minutes in the pan before inverting onto a serving tray.
- This cake is best the day it is made, but you can store leftovers in an airtight container at room temperature for up to 2 days.