This Pineapple Upside-Down Cheesecake Cake combines two classic desserts in one spectacular 9-inch, three-layer cake. It features a chilled vanilla cheesecake layer sandwiched between two pineapple juice-infused yellow cake layers, each baked over buttery brown sugar, pineapple rings, and maraschino cherries.
The result is a moist, tender, sweet-tart dessert with creamy cheesecake in every bite and a glossy pineapple topping that looks beautiful on a holiday table or birthday dessert spread. Plan on about 35–45 minutes of preparation, 55–65 minutes of baking, and 1 1/2–2 hours for cooling and chilling, yielding approximately 12–14 servings.
Jump to RecipeWhy You’ll Love This Recipe
This cake is designed for dessert lovers who cannot choose between a classic pineapple upside-down cake and a rich cheesecake. The contrast of textures makes it especially memorable: soft yellow cake, creamy cheesecake, buttery brown sugar syrup, and juicy pineapple all appear in one forkful.
The pineapple juice takes the place of some of the liquid normally used in a boxed cake, giving the layers a gentle tropical flavor without making the recipe complicated. Instant vanilla pudding also helps the cake stay moist and tender after chilling.
Although the finished cake looks like a bakery centerpiece, the method uses approachable ingredients and straightforward steps. If you enjoy fruit-forward desserts, you may also like this easy pineapple dessert for another creamy way to serve the same sunny flavor.
Ingredients You’ll Need
Gather the ingredients before beginning because this recipe has three separate components: the cheesecake layer, the pineapple cake layers, and the upside-down topping. Softened cream cheese is important for a smooth cheesecake batter, while well-drained pineapple keeps the cake from becoming soggy.
- For the cheesecake: 16 ounces softened cream cheese, 1/2 cup granulated sugar, 1 large egg, and 1/2 teaspoon vanilla extract.
- For the cake: one approximately 15.25-ounce box of yellow cake mix, one 3.4-ounce package of instant vanilla pudding mix, 1 cup reserved pineapple juice, 1/2 cup vegetable oil, and 3 large eggs.
- For the topping: 1/2 cup melted unsalted butter, 1 cup packed light brown sugar, one approximately 20-ounce can of pineapple rings, and 8–12 maraschino cherries.
- For serving: whipped cream and additional maraschino cherries are optional.
Use the juice from the canned pineapple first, then supplement it with water if the can does not provide a full cup. Set the juice aside before discarding or using any remaining liquid, and pat the pineapple rings dry with paper towels.
For another cream cheese dessert centerpiece, take a look at this banana cream cheesecake, which uses a similarly rich and comforting cheesecake base.
How to Make It Step-by-Step
Step 1: Heat the oven to 350°F and prepare the cheesecake pan. Grease a 9-inch springform pan, line its bottom with parchment, and lightly grease the parchment so the delicate layer can release cleanly.
Step 2: Beat the softened cream cheese and granulated sugar until completely smooth. Add the egg and vanilla extract, then mix only until incorporated; overbeating can add unnecessary air to the batter.
Step 3: Pour the cheesecake mixture into the prepared springform pan and bake for 25–30 minutes. The center should be set around the edges but still slightly soft, rather than dry or deeply browned.
Step 4: Let the cheesecake cool completely in the pan before chilling or briefly freezing it until firm. A cold, sturdy cheesecake layer is much easier to move and position between the cake layers without cracking.
Step 5: Grease two 9-inch round cake pans and divide the melted butter evenly between them. Sprinkle the brown sugar over the butter, spreading it as evenly as possible across the bottoms of both pans.
Step 6: Arrange the drained pineapple rings over the brown sugar mixture, cutting some rings as needed to fit the pans. Place a maraschino cherry in the center of each ring, keeping the pattern attractive because it will become the visible top of the cake.
Step 7: Combine the yellow cake mix, instant vanilla pudding mix, pineapple juice, vegetable oil, and eggs in a large bowl. Beat until the batter is smooth, following the general mixing method suggested on the cake mix package while using these listed ingredients.
Step 8: Divide the batter evenly between the two prepared pans. Pour slowly and carefully so the pineapple rings and cherries remain in place beneath the batter.
Step 9: Bake the cake layers at 350°F for approximately 25–30 minutes. Test the cake portion with a toothpick; it should come out clean when the layers are ready.
Step 10: Cool the cakes in their pans for about 10 minutes. Run a thin knife around each edge, place a rack over each pan, and invert carefully before allowing the layers to cool completely.
Step 11: Put one pineapple cake layer pineapple-side down on a serving plate. Set the chilled cheesecake layer on top, then add the second cake layer with its pineapple side facing up.
Step 12: Refrigerate the assembled cake until well chilled before slicing. Add whipped cream and extra cherries just before serving if desired.
Pro Tips for the Best Cake
Drain the pineapple thoroughly, but do not press it so aggressively that the rings break apart. Excess liquid can loosen the brown sugar topping and make the cake layers wet around the edges.
The cheesecake must be completely cold before assembly. If it feels soft or difficult to lift, chill it longer or briefly freeze it until firm enough to handle.
- Measure the pineapple juice after draining the can, then add water only as needed to make 1 cup.
- Use parchment on the springform pan bottom for easier cheesecake removal.
- Cool both pineapple cake layers fully before stacking so the cheesecake does not soften or slide.
- Run a knife around the cake pan edges before inverting each layer.
- Keep the pineapple arrangement centered and level for a polished presentation.
If you are planning a dessert table, this chocolate coconut almond poke cake offers a rich chocolate contrast to this bright pineapple creation.
Serving Suggestions
Serve each slice cold or just slightly cool from the refrigerator so the cheesecake center remains firm and creamy. A small spoonful of whipped cream beside the slice adds softness without covering the colorful pineapple topping.
For a special occasion, place the cake on a simple white or pale blue stand so the golden cake and red cherries stand out. Cut the slices with a warm, dry knife, wiping the blade between cuts for distinct layers.
The cake is sweet and substantial, so modest slices are ideal for a gathering of 12–14 people. Pair it with coffee, black tea, or a lightly sweetened iced tea to balance the buttery topping.
For another fun, layered dessert suitable for parties, try this Biscoff poke cake, especially when warm spice and cookie flavor are on the menu.
Storage and Make-Ahead Advice
Keep the assembled cake refrigerated because of the cheesecake layer. Cover it carefully and enjoy it well chilled; refrigerating it for several hours or overnight also improves the structure and makes slicing easier.
Prepare the cheesecake layer ahead of time and chill or briefly freeze it until firm, then make sure the pineapple cake layers are fully cooled before assembling. This staged approach removes pressure from the day you plan to serve the dessert.
Do not leave the assembled cake sitting at room temperature for an extended period. Add whipped cream shortly before serving so the garnish stays fresh and attractive.
For a different bake that is easy to portion for guests, consider this classic crumb cake as a simple companion dessert.
Pineapple Upside-Down Cheesecake Cake
Ingredients
Method
- Heat the oven to 350°F. Grease and parchment-line the bottom of a 9-inch springform pan, then beat the softened cream cheese and sugar until smooth. Add the egg and vanilla, mixing just until combined, and bake the cheesecake layer for 25–30 minutes until set but slightly soft in the center.
- Cool the cheesecake completely, then chill or briefly freeze it until firm enough to handle. Grease two 9-inch round cake pans and divide the melted butter and brown sugar between them.
- Arrange drained pineapple rings in the pans and place a maraschino cherry in the center of each ring. Reserve 1 cup of pineapple juice, adding water if necessary to reach the full amount.
- Beat together the yellow cake mix, instant vanilla pudding mix, pineapple juice, vegetable oil, and eggs until smooth. Divide the batter between the prepared pans without disturbing the pineapple arrangement.
- Bake the cake layers at 350°F for 25–30 minutes, until a toothpick inserted into the cake portion comes out clean. Cool them in the pans for about 10 minutes, run a knife around the edges, and invert them onto racks to cool completely.
- Place one pineapple cake layer pineapple-side down on a serving plate. Add the cold cheesecake layer, top with the second pineapple cake layer pineapple-side up, and refrigerate until thoroughly chilled before slicing.
Notes
Final Thoughts
This Pineapple Upside-Down Cheesecake Cake is a true celebration dessert, bringing together buttery caramelized fruit, tender pineapple cake, and a cool vanilla cheesecake center. Every layer has a purpose, and the finished combination is both nostalgic and special enough for birthdays, potlucks, and holiday meals.
The most important details are simple: reserve enough pineapple juice, drain the fruit well, chill the cheesecake until firm, and let the cake layers cool completely before stacking. Follow those points, refrigerate the completed cake thoroughly, and you will be rewarded with beautiful slices that hold their shape.
Finish each serving with whipped cream and a cherry for a classic presentation, then enjoy the bright pineapple flavor with every creamy, buttery bite.