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Copycat Pineapple Upside Down Cheesecake Recipe

ByCaroline
Jump to Recipe· 4.5 from 43 reviews

If you love the tropical charm of pineapple upside down cake and the creamy decadence of cheesecake, then you are going to absolutely adore this Copycat Pineapple Upside Down Cheesecake Recipe. It’s like having the best of both worlds in one stunning dessert that’s perfect for any occasion. I’m telling you, once you try this at home, you’ll want to make it again and again, especially with the juicy pineapples and that luscious cheesecake layer — it’s truly fan-freaking-tastic!

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Why This Recipe Works

  • Perfect Balance of Flavors: The tangy pineapple and sweet cherry topping complement the rich, creamy cheesecake beautifully.
  • Moist Cake Layers: The cake batter is perfectly tender and moist thanks to the blend of pineapple juice and sour cream.
  • Water Bath Baking: Baking the cheesecake in a water bath keeps it silky smooth and prevents cracks, giving you that professional finish at home.
  • Showstopping Presentation: The upside-down pineapple arrangement makes the dessert look gorgeous and inviting—no fancy decorating skills needed!
Copycat Pineapple Upside Down Cheesecake, pineapple upside down cake, pineapple cheesecake recipe, tropical cheesecake dessert, easy pineapple cheesecake - A two-layer round cake sits on a white marbled surface, with the bottom layer being a light brown sponge cake and the middle layer a thick, smooth cream that is pale yellow. The top layer is another light brown sponge with seven yellow pineapple rings evenly placed on it, each pineapple ring holding a small bright red cherry in the center. The cake looks moist and slightly shiny on top from the pineapple, and the overall shape is round and neatly stacked. In the background, there is a softly blurred aqua blue cloth, a white milk jug, and some out-of-focus flowers in soft pink and orange colors. Photo taken with an iphone --ar 2:3 --v 7 this …

Ingredients & Why They Work

This Copycat Pineapple Upside Down Cheesecake Recipe uses ingredients that bring out tropical sweetness and creamy richness and combine seamlessly for a truly indulgent dessert. Picking fresh or canned pineapple depending on your season can make a big difference, so here are a few tips on why these ingredients are key.

Copycat Pineapple Upside Down Cheesecake, pineapple upside down cake, pineapple cheesecake recipe, tropical cheesecake dessert, easy pineapple cheesecake - Flat lay of fresh cream cheese block, two whole brown eggs with clean shells, a small white bowl of granulated sugar, a small white bowl of light brown sugar, a small white bowl of sour cream, fourteen natural pineapple rings, fourteen bright red maraschino cherries, a small white bowl of melted unsalted butter, a small white bowl of pineapple juice, a small white bowl of milk, a small white bowl of vanilla extract, a white ceramic bowl with sifted all-purpose flour mixed with baking powder, baking soda, and salt, placed in perfect symmetry and realistic proportions on a clean white marble surface, soft natural light, photo taken with an iPhone, professional food photography style, fresh ingredients, white ceramic bowls, no bottles, no duplicates, no utensils, no packaging --ar 2:3 --v 7 --p m7354615311229779997
  • Cream Cheese: Softened to room temperature for a smooth cheesecake base that’s free of lumps.
  • Granulated and Brown Sugar: Brown sugar adds moisture and a subtle caramel note, while granulated sugar balances sweetness.
  • Eggs: They give structure and richness to the cheesecake and cake layers.
  • Sour Cream: Adds moisture and a slight tanginess, keeping the texture creamy and tender.
  • Pineapple Juice: Infuses every component with a fresh pineapple flavor that ties the layers together perfectly.
  • Vanilla Extract: A subtle warming flavor that enhances sweetness without overpowering.
  • Unsalted Butter: For richness in the cheesecake, the cake batter, and the caramelized topping.
  • Flour, Baking Powder, Baking Soda, Salt: Essential to get that fluffy yet moist cake texture.
  • Canned or Fresh Pineapple Rings and Maraschino Cherries: Classic, eye-catching toppings that soften beautifully under heat.
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Note: You’ll find the complete list of ingredients, along with their exact measurements, in the printable recipe card at the bottom of this post.

Make It Your Way

I love that this Copycat Pineapple Upside Down Cheesecake Recipe is so versatile — you can easily tweak it to suit your tastes or dietary needs. For example, I sometimes swap maraschino cherries for fresh strawberries when cherries feel too sweet for me, which adds a fresh twist.

  • Variation: Adding toasted coconut flakes on top gives an extra tropical crunch that’s delightful and a real crowd-pleaser at summer get-togethers.
  • Dairy-Free Tip: Use a plant-based cream cheese and substitute milk with almond or oat milk for a dairy-free version that still feels indulgent.
  • Extra Pineapple Kick: Stir some crushed pineapple into the cake batter for a more intense fruit flavor throughout.

Step-by-Step: How I Make Copycat Pineapple Upside Down Cheesecake Recipe

Step 1: Prep and Bake the Cheesecake Layer

I always start by warming up my cream cheese to room temperature — that’s crucial to avoid lumps! Then, with my hand mixer, I whip it smooth with granulated sugar. Adding eggs one at a time helps keep the batter silky. After mixing in sour cream, pineapple juice, and vanilla, I pour it all into a greased springform pan wrapped carefully in foil to prevent leaks. I bake it in a water bath, which is a game-changer for creamy, crack-free cheesecake. After baking, I let it cool completely on the counter before chilling overnight; trust me, this step makes slicing a breeze!

Step 2: Create the Glorious Pineapple Upside Down Topping

I melt butter and divide it between two cake pans, then sprinkle brown sugar on top — this forms the caramel base. I carefully arrange pineapple rings and place maraschino cherries right in the center of each pineapple slice for that classic look. Pro tip: Press down gently so the fruit sticks in place but don’t squish it, or you’ll get juice bleeding everywhere.

Step 3: Mix and Bake the Cake Layers

I sift all the dry ingredients together to keep the batter airy and smooth. Then in a separate bowl, I whisk the melted butter with brown and granulated sugars until creamy, adding eggs, sour cream, milk, pineapple juice, and vanilla next. Combining wet and dry ingredients gently with a spatula ensures no overmixing, which could make the cake dense. Pouring the batter over the pineapple topping evenly, I bake the layers until golden and a toothpick comes out clean. Baking times can vary, so keep an eye from 25 minutes onward.

Step 4: Assemble Your Copycat Pineapple Upside Down Cheesecake

This part’s so satisfying! I invert the first cake onto a cutting board and the second on your serving plate. Then carefully release the cheesecake from its springform pan — sometimes an offset spatula helps gently lift the edges. I layer the cheesecake on top of the first cake, and carefully add the second cake layer on top for that perfect triple-layer magic. You can serve it immediately or pop it in the fridge to chill for a few hours, which really helps the flavors meld together.

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Tips from My Kitchen

  • Room Temperature Ingredients: Always bring cream cheese, eggs, and sour cream to room temp before mixing — it makes all the difference for silky batter.
  • Foil Wrapping: Wrapping the springform pan in heavy-duty foil keeps your water bath mess-free and prevents leaks into the roasting pan.
  • Gentle Mixing: Don’t overbeat the cheesecake batter; too much air means cracks and bubbles after baking.
  • Invert with Care: When flipping the cake layers, use a flat surface and lift slowly so fruit and caramel stay perfectly in place.

How to Serve Copycat Pineapple Upside Down Cheesecake Recipe

Copycat Pineapple Upside Down Cheesecake, pineapple upside down cake, pineapple cheesecake recipe, tropical cheesecake dessert, easy pineapple cheesecake - The image shows a slice of pineapple upside-down cake being lifted by a fork. The cake slice has three layers: the top yellow layer is a round pineapple ring with a bright red cherry in the center, the middle layer is light and creamy with a smooth texture, and the bottom layer is a golden brown cake with small chunks of pineapple embedded. The full cake below has similar layers and looks moist and soft. The scene is set on a white marbled surface, with a blurry background featuring pink flowers and a glass bottle of milk. Photo taken with an iphone --ar 2:3 --v 7

Garnishes

I almost always add a dollop of freshly whipped cream on each slice — the light airy cream balances the dense cheesecake so well. Sometimes, I sprinkle toasted coconut flakes or a bit of finely chopped fresh mint for an extra fresh touch that looks gorgeous and adds that wow factor.

Side Dishes

This dessert pairs wonderfully with a simple cup of coffee or a tropical iced tea. For a more festive spread, I like serving it alongside light fruit salads or a scoop of vanilla bean ice cream for guests who want extra indulgence.

Creative Ways to Present

For parties, I sometimes assemble mini layers in clear glasses as individual servings — layers of cake, cheesecake, and pineapple stacked up so everyone gets a custom portion. Flipping the cake onto a colorful serving platter and garnishing with edible flowers also makes it feel extra special for celebrations.

Make Ahead and Storage

Storing Leftovers

This cheesecake keeps beautifully in the fridge for up to 4 days. I store leftovers in an airtight container or wrapped tightly in plastic wrap to keep it moist and fresh. Just be sure to keep it chilled, as the cheesecake won’t hold up well at room temperature for long.

Freezing

If you want to freeze slices, I recommend wrapping them individually in plastic wrap and then placing them in a freezer-safe container. When I’ve tried this, I usually thaw overnight in the fridge — the texture stays nearly as good as fresh, just maybe a touch less creamy.

Reheating

Since this is a cheesecake, I prefer to serve leftovers cold or at room temperature. But if you want it a bit warmer, letting slices sit out for about 30 minutes works best — skip the microwave to avoid drying out the cake layers.

FAQs

  1. Can I use fresh pineapple instead of canned for the Copycat Pineapple Upside Down Cheesecake Recipe?

    Absolutely! Fresh pineapple works wonderfully and adds a bright, natural sweetness that I love. Just be sure to slice the pineapple rings evenly and drain any excess juice so your topping doesn’t get soggy.

  2. Why is the cheesecake baked in a water bath?

    Baking the cheesecake in a water bath helps regulate the heat and moisture around the pan, which prevents cracks and ensures your cheesecake stays creamy and smooth. It’s a simple step that makes a huge difference in texture.

  3. Can I make this recipe ahead of time for a party?

    Definitely! In fact, making it the day before is ideal. The flavors deepen and the layers set perfectly after chilling overnight, so it’s a great make-ahead dessert for any gathering.

  4. What’s the best way to avoid the pineapple sliding off when flipping the cake?

    Make sure you lightly press the pineapple and cherries into the brown sugar and butter mixture before pouring the batter over. Also, invert the cake slowly and on a completely flat surface to keep the toppings intact.

  5. Can I use boxed yellow cake mix instead of making the cake batter from scratch?

    You could, but making the batter yourself allows you to infuse it with pineapple juice and sour cream for that perfect texture and flavor harmony, which boxed mixes can’t quite replicate. It’s worth the little extra effort!

Final Thoughts

This Copycat Pineapple Upside Down Cheesecake Recipe really holds a special place in my heart — it’s one of those desserts that brings a bit of sunshine and celebration to any day. Whether you’re enjoying it as a weekend treat or impressing friends at a dinner party, it’s bound to get compliments and maybe a few “Wow, did you make this?” moments. I can’t recommend making this enough — give it a go, and I promise it’ll become a favorite in your recipe box, too!

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Copycat Pineapple Upside Down Cheesecake Recipe

5 Stars 4 Stars 3 Stars 2 Stars 1 Star 4.5 from 43 reviews
  • Author: Caroline
  • Prep Time: 20 minutes
  • Cook Time: 1 hour 35 minutes
  • Total Time: 7 hours 40 minutes
  • Yield: 12 servings
  • Category: Dessert
  • Method: Baking
  • Cuisine: American
  • Diet: Vegetarian
Print Recipe

Description

This Copycat Pineapple Upside Down Cheesecake is a delightful fusion dessert that combines rich, creamy pineapple-flavored cheesecake with the classic pineapple upside-down cake layers. Featuring a moist cake base topped with caramelized pineapple rings and cherries, this indulgent treat is perfect for special occasions or a sweet indulgence.

Ingredients

Pineapple Cheesecake

  • 16 ounces cream cheese room temp
  • 1/2 cup granulated sugar
  • 2 large eggs
  • 1/2 cup sour cream
  • 2 tablespoons pineapple juice
  • 1 teaspoon vanilla extract

Pineapple Upside-Down Cake Topping

  • 1/2 cup unsalted butter melted
  • 1 cup packed light brown sugar
  • 14 slices canned or fresh pineapple rings
  • 14 maraschino cherries

Pineapple Upside-Down Cake Batter

  • 1 1/2 cup + 3 tablespoons all-purpose flour sifted
  • 1/2 teaspoon baking powder
  • 1/4 teaspoon baking soda
  • 1/2 teaspoon salt
  • 1/2 cup unsalted butter melted
  • 3/4 cup light brown sugar packed
  • 1/4 cup granulated sugar
  • 1 large egg
  • 1/4 cup sour cream
  • 1/2 cup milk
  • 1/4 cup pineapple juice
  • 1 tablespoon vanilla extract

Instructions

  1. Prepare Cheesecake Batter: Preheat the oven to 325°F. Grease a 9-inch springform pan, wrap it in heavy-duty foil, and set aside. In a large bowl, whip the cream cheese and 1/2 cup granulated sugar with an electric hand mixer until smooth. Mix in the eggs one at a time until fully combined, scraping down the sides as needed. Add the sour cream, pineapple juice, and vanilla extract; mix until completely smooth. Pour the batter into the prepared pan and place it into a large roasting dish.
  2. Bake Cheesecake in Water Bath: Reduce oven temperature to 300°F. Fill the roasting pan halfway up the sides of the cheesecake pan with hot water from the tap. Bake for 45 minutes, then turn off the oven and leave the cheesecake inside for an additional 20 minutes to set. Remove the cheesecake from the oven and roasting pan, let cool to room temperature, cover with plastic wrap, and refrigerate for at least 8 hours or overnight.
  3. Prepare Cake Topping: Divide melted butter equally between two 9-inch cake pans. Sprinkle 1/2 cup packed brown sugar equally into each pan. Arrange the pineapple rings and maraschino cherries on top of the sugar mixture as shown or desired, setting aside for later.
  4. Make Cake Batter: Preheat oven to 350°F. In a large bowl, whisk together sifted flour, baking powder, baking soda, and salt. In another bowl, whisk melted butter, brown sugar, and granulated sugar until smooth. Add egg, sour cream, milk, pineapple juice, and vanilla extract; whisk until combined. Combine wet mixture with dry mixture and stir gently until no lumps remain.
  5. Bake Cake Layers: Evenly divide the batter between the two prepared pans on top of the pineapple and cherries. Smooth the tops carefully without disturbing the fruit. Bake for 30 minutes or until a toothpick inserted into the center comes out clean and the cakes are golden brown. Cool cakes in pans on wire racks for 10 minutes.
  6. Assemble the Cake: Invert one pineapple upside-down cake layer onto a flat surface like a cutting board. Remove the cheesecake carefully from the springform pan, lifting it off the base using a tool such as an offset spatula. Place the cheesecake on top of the first inverted cake layer. Invert the second pineapple upside-down cake layer and place it on top of the cheesecake. Optionally, refrigerate until ready to serve and garnish with whipped cream if desired.

Notes

  • Always use room temperature cream cheese, eggs, and sour cream to achieve a smooth and creamy cheesecake batter.
  • Baking the cheesecake in a water bath helps prevent cracks and ensures a silky texture.
  • Mix cheesecake filling on low speed to avoid incorporating excess air that could cause cracks.
  • Allow the cheesecake to cool completely at room temperature before refrigerating to help it set properly.
  • When inverting the pineapple upside-down cake layers, do so gently to keep pineapple rings and cherries in place.
  • Refrigerate the fully assembled cake for a few hours to enhance flavor melding and cake stability before serving.

Nutrition

  • Serving Size: 1 slice (1/12 of cake)
  • Calories: 450 kcal
  • Sugar: 35 g
  • Sodium: 250 mg
  • Fat: 28 g
  • Saturated Fat: 17 g
  • Unsaturated Fat: 9 g
  • Trans Fat: 0 g
  • Carbohydrates: 40 g
  • Fiber: 1 g
  • Protein: 6 g
  • Cholesterol: 110 mg

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