Quick Recipe Version (TL;DR)
Quick Ingredients
- 2 cans (20 oz / 567 g each) pineapple rings in juice, drained (reserve 1/2 cup juice)
- 1 small jar maraschino cherries, drained and patted dry
- 2 3/4 cups (620 g) unsalted butter, softened, divided, plus extra for greasing
- 2 3/4 cups (330 g) all-purpose flour
- 1 3/4 cups (350 g) granulated sugar + 1 1/4 cups (250 g) light or dark brown sugar, divided
- 4 large eggs, room temperature
- 1 cup (240 ml) whole milk, room temperature
- 4 cups (480 g) powdered sugar
- 2 1/2 tsp baking powder, 1/2 tsp baking soda, 1 tsp fine salt
- 2 tsp vanilla extract
- 1/2 cup (120 ml) neutral oil (canola or vegetable)
Do This
- 1. Heat oven to 350°F (175°C). Grease three 8-inch round cake pans and line bottoms with parchment. Melt butter and brown sugar in each pan and arrange pineapple rings and cherries in a single layer.
- 2. Whisk flour, baking powder, baking soda, and salt. In another bowl, mix milk and reserved pineapple juice.
- 3. Cream butter, oil, granulated sugar, and brown sugar. Beat in eggs and vanilla, then alternately add dry ingredients and milk mixture. Divide batter over the pineapple in the pans.
- 4. Bake 28–32 minutes until golden and a toothpick comes out clean. Cool 15 minutes, then invert layers onto wire racks. Cool completely.
- 5. Beat softened butter and brown sugar until fluffy. Gradually add powdered sugar, vanilla, salt, and enough cream or milk to make a smooth brown sugar buttercream.
- 6. Caramelize a few extra pineapple rings in a skillet with butter and brown sugar until deep golden. Cool.
- 7. Stack cake layers pineapple-side up with buttercream between. Frost the sides and top, then decorate with caramelized pineapple and cherries.
Why You’ll Love This Recipe
- All the nostalgic flavor of classic pineapple upside-down cake, transformed into a show-stopping layer cake.
- Rich, buttery vanilla cake stays incredibly moist thanks to pineapple juice and juicy fruit.
- Brown sugar buttercream adds a caramel note that pairs perfectly with pineapple and cherries.
- Perfect for birthdays and celebrations when you want something retro, playful, and impressive.
Grocery List
- Produce: Canned pineapple rings in juice, optional extra fresh or canned pineapple for topping, maraschino cherries.
- Dairy: Unsalted butter, whole milk, heavy cream or milk (for frosting), large eggs, optional cream cheese (for variation).
- Pantry: All-purpose flour, granulated sugar, light or dark brown sugar, powdered sugar, baking powder, baking soda, fine salt, vanilla extract, neutral oil (canola or vegetable), nonstick cooking spray or extra butter for pans.
Full Ingredients
For the Pineapple Upside-Down Topping (for 3 layers)
- 6 tbsp (85 g) unsalted butter
- 3/4 cup (150 g) packed light or dark brown sugar
- 15–18 pineapple rings (from about 2 cans, 20 oz / 567 g each), well drained
- 30–40 maraschino cherries, drained and patted very dry (you may not use the entire jar, but it is good to have extras)
For the Buttery Pineapple Cake Layers
- 2 3/4 cups (330 g) all-purpose flour, spooned and leveled
- 2 1/2 tsp baking powder
- 1/2 tsp baking soda
- 1 tsp fine sea salt
- 3/4 cup (170 g) unsalted butter, softened to room temperature
- 1/2 cup (120 ml) neutral oil (canola or vegetable)
- 1 3/4 cups (350 g) granulated sugar
- 1/2 cup (100 g) packed light brown sugar
- 4 large eggs, at room temperature
- 2 tsp pure vanilla extract
- 1 cup (240 ml) whole milk, at room temperature
- 1/2 cup (120 ml) reserved pineapple juice from the cans (top up with water if you are slightly short)
For the Brown Sugar Buttercream
- 1 1/2 cups (340 g) unsalted butter, very soft but not melted
- 1/2 cup (100 g) packed light or dark brown sugar
- 4 cups (480 g) powdered sugar, sifted
- 1/4–1/3 cup (60–80 ml) heavy cream or whole milk, plus more as needed
- 2 tsp pure vanilla extract
- 1/4 tsp fine sea salt (to taste)
For the Extra Caramelized Pineapple Decoration (Topper)
- 4–6 additional pineapple rings (fresh or canned), very well drained and patted dry
- 2 tbsp (28 g) unsalted butter
- 3 tbsp (40 g) packed light or dark brown sugar
- Extra maraschino cherries for garnish (optional)
Optional: Cream Cheese Frosting Alternative
If you prefer a tangier frosting instead of brown sugar buttercream, you can make a simple cream cheese version:
- 8 oz (225 g) full-fat cream cheese, softened
- 1/2 cup (115 g) unsalted butter, softened
- 4 cups (480 g) powdered sugar, sifted
- 2 tsp vanilla extract
- Pinch of salt
Step-by-Step Instructions
Step 1: Prepare the pans and arrange the pineapple topping
Preheat your oven to 350°F (175°C). Grease three 8-inch (20 cm) round cake pans generously with butter or nonstick spray. For extra insurance, line the bottoms with parchment circles and grease the parchment as well.
Divide the 6 tablespoons (85 g) butter among the three pans (2 tablespoons per pan). Place the pans in the warm oven for 2–3 minutes, just until the butter melts. Remove from the oven and swirl each pan so the bottom is evenly coated.
Sprinkle 1/4 cup (50 g) brown sugar into each pan over the melted butter, spreading it into an even layer. Arrange 5–6 pineapple rings in a single layer over the sugar in each pan. Put one maraschino cherry in the center of each ring and, if you like, tuck extra cherries into gaps between rings. Set the pans aside while you make the batter.
Step 2: Mix the dry and wet ingredients for the cake
In a medium bowl, whisk together the flour, baking powder, baking soda, and salt until well combined. This helps the leavening distribute evenly.
In a separate measuring jug or bowl, stir together the whole milk and reserved pineapple juice. Both should be at room temperature so they blend smoothly into the batter. Set both bowls aside.
Step 3: Make the buttery cake batter
In a large mixing bowl (or in the bowl of a stand mixer fitted with the paddle attachment), beat the softened butter, neutral oil, granulated sugar, and 1/2 cup brown sugar on medium-high speed for 3–4 minutes, until the mixture is very light and fluffy. Scrape down the bowl once or twice as needed.
Add the eggs one at a time, beating well after each addition until fully incorporated. Mix in the vanilla extract.
Turn the mixer to low. Add about one-third of the flour mixture, followed by half of the milk-pineapple juice mixture. Repeat with another third of the flour, the remaining liquid, and then the final third of the flour. Mix just until the batter is smooth and no dry streaks remain. Do not overmix, or the cake may become dense.
Step 4: Bake and invert the pineapple layers
Divide the batter evenly among the three prepared pans, gently smoothing the tops with an offset spatula or the back of a spoon. The batter will cover the pineapple and cherries.
Bake at 350°F (175°C) for 28–32 minutes, or until the cakes are golden, pulling slightly away from the edges, and a toothpick inserted into the center of each comes out clean or with a few moist crumbs (but no wet batter).
Transfer the pans to a wire rack and cool for exactly 15 minutes. While the cakes are still warm (this is important so the caramelized topping releases), run a thin knife around the edges of each pan to loosen. Place a cooling rack or plate over one pan and, using oven mitts, carefully invert. Tap the bottom of the pan gently and lift it off. Peel away parchment if you used it. Repeat with the remaining layers. Allow all three layers to cool completely, pineapple side up, before frosting (about 45–60 minutes).
Step 5: Make the brown sugar buttercream
In a large bowl, beat the softened butter and brown sugar together on medium-high speed for 3–5 minutes, until very light, fluffy, and slightly paler. This extra beating time helps the brown sugar begin to dissolve and become less gritty.
Reduce the speed to low and add the sifted powdered sugar 1 cup at a time, mixing well and scraping the bowl as needed. The mixture will be quite thick.
Add the vanilla and salt. Then slowly pour in 1/4 cup (60 ml) of heavy cream or milk while mixing on low. Increase the speed to medium-high and beat for 2–3 minutes, until the frosting is smooth, airy, and spreadable. If it is too thick, add more cream or milk 1 tablespoon at a time. If it is too soft, add a little more powdered sugar. Set aside at cool room temperature until ready to use.
For the cream cheese frosting alternative: Beat softened cream cheese and butter together until smooth and creamy. Gradually add powdered sugar, vanilla, and salt, and beat until fluffy. Use in the same way as the buttercream.
Step 6: Caramelize extra pineapple rings for the top decoration
While the cake layers cool, prepare the decorative pineapple topper. In a large nonstick or stainless skillet, melt 2 tablespoons (28 g) butter over medium heat. Stir in 3 tablespoons (40 g) brown sugar until it is dissolved and bubbling.
Add 4–6 pineapple rings in a single layer. Cook for 3–4 minutes on the first side, then carefully flip and cook another 3–4 minutes, until the slices are deep golden, glossy, and lightly caramelized around the edges. Adjust the heat as needed so the sugar does not burn.
Transfer the caramelized rings to a parchment-lined plate or tray to cool completely. The caramel will thicken as it cools. Set aside for decorating the top of the cake.
Step 7: Level (if needed) and assemble the layers
Once the cake layers are completely cool, check whether the bottoms (the non-pineapple sides) are level. If any domes are quite high, you can gently trim them off with a long serrated knife to create flat surfaces for stacking. Work slowly and keep the pineapple-topped surfaces intact.
Place a small dollop of buttercream in the center of your serving plate or cake stand to act as glue. Set the first layer in the center of the stand, pineapple side up. Spread about 3/4 to 1 cup of buttercream over the cake, staying just shy of the edges.
Carefully place the second layer on top, again pineapple side up, aligning the edges. Repeat with another layer of buttercream. Add the final cake layer, pineapple side up. At this point, the pineapple patterns should be visible on the top and hidden between the layers.
Step 8: Frost, decorate, and serve
Use a thin layer of buttercream to crumb-coat the sides of the cake (a light layer that traps crumbs). Chill the cake for 15–20 minutes if your kitchen is warm or if the frosting feels soft.
After chilling, frost the sides and top of the cake with the remaining buttercream, smoothing it with an offset spatula or creating rustic swirls. Aim to keep the pineapple design on the very top mostly visible around the center where you will add extra decoration.
Arrange the cooled caramelized pineapple rings on top of the cake: you can cluster them in the center, fan them out, or slightly overlap them. Add extra maraschino cherries in the centers or nestle them between rings for a bright pop of color. If any caramel from the pan is still pourable, drizzle a little over the fruit for shine.
Let the finished cake sit at room temperature for at least 20–30 minutes before slicing so the buttercream softens and the flavors meld. Slice with a sharp, thin knife, wiping the blade between cuts for the cleanest layers.
Pro Tips
- Dry your fruit well. Pat both pineapple rings and cherries dry with paper towels so they do not make the cake soggy or bleed color into the batter.
- Invert while still warm. Turning the cakes out after about 15 minutes of cooling helps the caramelized topping release cleanly from the pan.
- Use room-temperature ingredients. Soft butter, room-temperature eggs, and milk blend more easily and help create a light, even crumb.
- Do not overmix the batter. Once you add the flour, mix just until combined to keep the cake tender and prevent it from becoming tough.
- Chill briefly for clean layers. If the cake or frosting feels soft, a short chill before the final coat of frosting and before slicing will give neater edges and sharper layers.
Variations
- Cream Cheese Frosting Version: Swap the brown sugar buttercream for the cream cheese frosting listed above. It gives a tangy contrast to the sweet pineapple and caramelized sugar.
- Coconut Twist: Add 1/2 cup (40 g) unsweetened shredded coconut to the cake batter, and/or press toasted coconut into the sides of the frosted cake for extra tropical flavor and texture.
- Simple Party Sheet Cake: Bake the batter and topping in a single greased 9×13-inch (23×33 cm) pan at 350°F (175°C) for 35–40 minutes. Invert once, then frost only the top with a thinner layer of buttercream.
Storage & Make-Ahead
Because this cake contains fresh fruit and a butter-based frosting, it keeps best in a cool place. Store the fully assembled cake, covered, in the refrigerator for up to 3 days. For the best texture and flavor, let slices or the whole cake sit at room temperature for 30–45 minutes before serving so the buttercream softens.
You can bake the cake layers up to 1–2 days ahead. Once completely cool, wrap each layer tightly in plastic wrap and store at room temperature or in the refrigerator. Frosting can be made 1–2 days in advance and stored in an airtight container in the refrigerator; bring to room temperature and rewhip briefly before using. The caramelized pineapple topper is best made the day you assemble the cake, but it can sit at room temperature for several hours. To freeze, wrap individual unfrosted layers well and freeze for up to 2 months; thaw overnight in the refrigerator before assembling.
Nutrition (per serving)
Approximate values for 1 slice (1/12 of the cake), using brown sugar buttercream: about 650 calories; 32 g fat; 18 g saturated fat; 90 g carbohydrates; 58 g sugars; 6 g protein; 1 g fiber; 360 mg sodium. These numbers are estimates and will vary based on exact ingredients and portion sizes.
