pineapple upside-down cheesecake

Pineapple Upside Down Cheesecake tastes like a classic Pineapple Upside Down Cake in cheesecake form! Ultra creamy brown sugar cheesecake is baked over a crisp graham cracker crust, and filled with a layer of caramelized pineapple filling. Top this stunning dessert with more caramelized pineapple filling, swirls of vanilla whipped cream, and maraschino cherries.

this recipe

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Why you’ll love this Pineapple Upside Down Cheesecake:

• Ultra Creamy Pineapple Cheesecake – My ultra creamy cheesecake base is incredibly simple to make and comes together quickly.
• Pineapple Filling & Topping – This cheesecake is topped & stuffed with juicy, caramelized pineapple slices!
• Crisp Graham Crust – The whole dessert bakes atop a perfectly crisp, buttery graham cracker crust.
• Whipped Cream & Cherries – This cheesecake wouldn’t be complete without whipped cream and maraschino cherries on top – just like on a classic pineapple upside down cake!

Ingredient Overview:

As always, the full recipe with measurements & directions can be found in the recipe card at the bottom of this post. Use the table of contents (back at the top, below the first image, to navigate).

• Cream Cheese – Use full fat cream cheese, in the block style. This needs to come to room temperature before you bake.
• Brown sugar – I love the depth of flavor that dark brown sugar lends here, but light brown sugar works as well. You can even use granulated sugar in a pinch, but brown sugar really gives that pineapple upside down cake taste!
• Eggs – Use large eggs at room temperature.
• Sour Cream – Use full fat sour cream, at room temperature.
• Vanilla extract – Use real vanilla extract for best results.
• Pineapple – I found it easier to buy canned pineapple rings for this recipe, so I didn’t have to wait for 3 large pineapples to ripen each time I needed to test this. But, you can use either! Just be sure to use ripe pineapples if using fresh. A ripe, fresh pineapple should feel firm but not rock hard, and not soft. It should be turning yellow on the outside, and you should smell a ripe pineapple aroma when you sniff the base of the pineapple. You should also be able to pluck one of the leaves without too much effort. (In my opinion, the fresh pineapple is better saved for my Grilled Pineapple!)
• Graham Cracker Crumbs – I used ready made graham cracker crumbs for this recipe. You can make your own by pulsing whole graham crackers in the food processor until you have fine crumbs. If using this option, you may need 1-2 tbsp additional butter in the crust mixture for things to come together.

Recipe Substitutions & Variations:

• Gluten-free – Use gluten-free graham crackers to make this recipe gluten-free!
• Dairy-free – I have not experimented with dairy-free cheesecakes so I can’t recommend anything with confidence here, except to check out a reputable vegan baking blog, like The Banana Diaries or Little Blog of Vegan!
• Graham Crackers – Digestive biscuits or something similar would be comparable to graham crackers if you don’t live in the U.S.
• Sour cream – You can use full fat plain greek yogurt or heavy cream in place of the sour cream.
• Fewer Steps: Pinched for time? Just make half the pineapple filling, and use it only on top.
• Piña Colada Cheesecake – Add 2-4 tbsp of coconut rum to the cheesecake batter (add it with the sour cream and vanilla) and 1-3 tbsp to the pineapple filling (add it at the end, after it’s been fully cooked) to make a fun adults only twist on this Pineapple Cheesecake!
• Cool Whip – Serve with dollops of cool whip if you don’t have time to make the whipped cream.
• Small Cheesecake – For a smaller, easy dessert – halve the recipe, and bake the batter in a 9-inch prepared graham cracker crust, with no pineapple added to the center. Top the baked & chilled cheesecake with a 1/3 batch of the pineapple filling. (You can find these in the baking aisle at most grocery stores.)

How to Make this Pineapple Upside Down Cheesecake:

Step 1: Make the Caramelized Pineapple Filling & Topping. Cook pineapple chunks, brown sugar, and pineapple juice together until the juices have reduced.

Add the cornstarch slurry (this is a fancy term for a mixture of corn starch dissolved in water) and cook 1-2 minutes more, until thickened. Stir in the vanilla and let cool completely.

(Pictured is half a batch of what the recipe calls for, so you’ll want to use a larger pot than this.)

Step 2: Make the Crust. Stir together graham cracker crumbs and melted butter. Press this into the bottom and up the sides of the springform pan and bake for 10 minutes.

Step 3: Make the Cheesecake Batter.  In a large bowl, beat your cream cheese on high speed with an electric mixer, until creamy. (You can also do this in the bowl of a stand mixer, fitted with the paddle attachment.)

Then, mix in the sugar, eggs, vanilla, and sour cream. You’ll have a silky batter. If there are a few tiny lumps, that’s ok.

Step 4: Assemble the Cheesecake. Pour half the batter into the baked crust. Spoon on the pineapple filling, then pour the remaining batter over, spreading it evenly with an offset spatula.

Step 5: Bake Cheesecake. Bake the cheesecake inside of a 10-inch cake pan inside of a roasting pan filled with 2 inches of boiling water. Bake at 350 as directed in the recipe card below.

Step 6: Decorate the Cheesecake. Top the chilled cheesecake with pineapple compote, whipped cream, and place cherries on top of the whipped cream!

Serving + Storing:

Once decorated, slice & serve immediately! Store the leftover cheesecake in an airtight container in the fridge for 2-3 days. If you love pineapple, try my Piña Colada Cake or my Pineapple Carrot Cake next!

Expert Success Tips:

• Forgot to Bring Ingredients to Room Temp? Bring your cold ingredients out about 30-45 minutes ahead of baking so they can come to room temperature. If you forget, here’s my trick. Place eggs in a bowl of warm water to bring them to room temperature quickly. Meanwhile, place two blocks of cream cheese on a plate, and microwave for 5-6 seconds, flip, & repeat. Repeat with the remaining two blocks. For sour cream, add to a bowl and heat for 5-6 seconds, stirring, then repeat once, until just at room temperature.
• Scrape the Bowl – Scrape the bowl, getting down to the very bottom, between the addition of each ingredient in this recipe. Little lumps of cream cheese love to hide down there!
• Oven Thermometer – An oven thermometer will tell you if your oven is actually running at the temperature you set it to. Your oven may not be accurate. Accurate oven temperature is crucial for most bakes, so I leave an oven thermometer in at all times to keep an eye on my oven’s calibration.
• Kitchen Scale – A food scale is the best way to make sure your ingredients are at the proper weight, since amounts will vary based on how you measure, as well as the measuring cup you use, as they are not standardized.

FAQs:

Special Tools:

• Springform Pan – This lemon meringue cheesecake recipe uses a 9-inch springform pan.
• 10-Inch Cake Pan – Use a 10-inch cake pan as your barrier between the cheesecake pan and the water bath in the roasting pan.
• Roasting Pan – A roasting pan is essential for a water bath when making cheesecake.

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More Favorite Cheesecake Recipes:

• Key Lime Pie Cheesecake
• Lemon Meringue Pie Cheesecake
• Salted Caramel Crème Brûlée Cheesecake
• Biscoff Cheesecake
• Triple Nutella Cheesecake
• Lemon Blueberry Cheesecake

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