Pineapple-Upside Down Cheesecake

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A crave-worthy combination of two amazing desserts, this Pineapple Upside Down Cheesecake combines juicy baked pineapple in a brown sugar topping with a decadent cheesecake base.

The Perfect Pineapple Dessert with Creamy, Homemade Cheesecake

Have you ever tried pineapple upside-down cake? If so, then you know the classic recipe is one addictive treat. It’s a tender vanilla cake, lightly sweetened with added pineapple juice, and baked over a scrumptious layer of pineapple, butter, and brown sugar. When the cake is inverted onto a plate, the pineapple layer ends up on top – decorative and delicious.

Well, in this recipe, we’re taking that same idea and applying it to cheesecake! Pineapple and real, made-from-scratch cheesecake are a dreamy combination, especially with buttery graham cracker crust, maraschino cherries, and that classic brown-sugar-butter topping.

Ingredients

The ingredients for homemade cheesecake include plenty of full-fat cream cheese, as well as sour cream, sugar, and vanilla extract. Since this is a pineapple upside-down cheesecake, you’ll also need canned pineapple rings, pineapple juice (from the can), and more. Here’s the full list:

For the Pineapple Layer

• Butter: The butter needs to be melted – you can do this by microwaving the butter for 15 seconds at a time and stirring in between, or just melt it in a small saucepan over low heat.
• Brown Sugar: You can use either light or dark brown sugar. I used light brown.
• Pineapple Rings: You’ll need about 10 pineapple rings. Save the juice from the pineapple can to flavor the cheesecake layer.
• Maraschino Cherries: Colorful maraschino cherries go right into the center of the pineapple rings.
• Graham Cracker Crumbs: You can use ready-made graham cracker crumbs, or crush up the graham crackers yourself.
• Sugar: A small amount of granulated sugar is used to sweeten the graham cracker crust.

For the Cheesecake Layer

• Cream Cheese: The cream cheese should be softened to room temperature.
• Light Brown Sugar
• Flour: All-purpose flour, not self-rising.
• Sour Cream: The sour cream should also be at room temperature.
• Pineapple Juice: Reserved from the can of pineapple rings.
• Vanilla: Pure vanilla extract is best.
• Eggs: Use large, whole eggs.

Step-by-Step Instructions

Making cheesecake isn’t hard, but it does involve a number of important steps. And for this recipe, you also need to make the pineapple “crust,” which will be the pineapple topping when you invert the cheesecake onto a serving platter. Let’s take a look at each step.

Make the Crust

The first layer of this dish is the pineapple crust. Here’s how to make it, and how to get the springform pan ready for baking in its water bath.

1. Prepare Your Pan and Preheat the Oven. Before you start making the cheesecake, get the oven preheating to 300°F. That temperature may seem low, but it is important for baking the delicate cheesecake mixture without overcooking it. Next, line the bottom of a 9-inch springform pan with parchment paper, and grease the sides of the pan with butter, oil, or a little bit of baking spray.
2. Add the Butter, Brown Sugar, Pineapple, and Cherries. Now it’s time to make the pineapple portion of this recipe. Mix together four tablespoons of melted butter with the brown sugar, and spread this evenly in the bottom of the pan, using a spoon. Pat the slices of pineapple dry with a paper towel, and then arrange them in the brown sugar mixture and along the sides of the pan. Add the cherries.
3. Top with Graham Cracker Crumb Crust. Finally make a mixture of graham cracker crumbs, sugar, and the remaining three tablespoons of butter. Spread and pat this evenly over the previous layers, gently pressing it down in and around the pineapple rings and cherries.
4. Prepare Your Pan for the Water Bath. It’s important to bake homemade cheesecakes like this in a bain-marie, or water bath. The water creates steam and slightly insulates the pan while it bakes, helping prevent those dreaded cracks. However, springform pans sometimes leak, which means water could get into the cheesecake if you don’t wrap the pan. Many people wrap the pan in one large sheet of foil, with the edges pulled up to the top of the pan. I like to use crockpot liners for more reliable protection – see my easy tutorial for wrapping a springform pan here.

Make the Cheesecake

With the pineapple crust done, set the pan aside, and let’s get started on the cheesecake filling.

1. Beat the Cream Cheese, Brown Sugar, and Flour. In the bowl of a stand mixer, or using a large mixing bowl and a hand mixer, combine the cream cheese, brown sugar, and flour. You may want to sift the flour to prevent lumps. Beat these ingredients on LOW speed until they’re well combined and smooth. Using a low speed reduces the amount of air in the mixture, which keeps the texture of the final cheesecake silky and crack-free.
2. Add the Sour Cream, Pineapple, and Vanilla. Scrape down the sides of the bowl, and add the sour cream, the reserved pineapple juice, and the vanilla extract. Mix again on LOW until the mixture is well combined and smooth.
3. Add the Eggs. Let the mixture run on LOW while you add the eggs one by one. Wait until the mixture is fully combined before adding the next egg. Scrape down the sides of the bowl, and give the mixture one last gentle mix to make sure it’s fully incorporated.
4. Pour the Cheesecake into the Pan and Set Up the Water Bath. Gently pour the entire batch of cheesecake batter over your pineapple crust. Set the springform pan inside another larger pan, like a brownie pan or a roasting pan. Set this on your oven rack, and pour water into the outer pan. The water should come about halfway up the sides of your springform pan. DO NOT let the water go over your foil layer, or it might seep into the cheesecake!
5. Bake and Cool. Bake the cheesecake for about one hour, until the center is set, but still jiggly. I baked mine for 1 hour and 5 minutes, but your oven may take slightly more or less time, depending. Once the cheesecake is baked, turn the oven off, but leave the cheesecake in the oven with the door closed for another half hour to begin cooling down. After half an hour is up, crack the oven door, and let the cheesecake continue cool in the cracked oven for 30 minutes more.
6. Chill. Now your cheesecake is ready to chill! Take it out of the oven and water bath, and remove the wrappings from the springform pan. Set it in the refrigerator for 5 – 6 hours, or overnight.
7. Plate and Serve. When you’re ready to serve your cheesecake, remove the sides of the springform pan, and gently lay a serving platter on top of the cheesecake. Turn the cheesecake and plate over. Remove the bottom of the springform pan, and peel away the parchment to reveal the pineapple layer. Slice and serve.

Tips for Success

Homemade cheesecake is such a rewarding treat to make, and these easy tips will help make sure your pineapple upside-down cheesecake turns out perfectly. I hope you love this luscious, fruity cheesecake as much as I do!

• Use Full-Fat Ingredients: While low-fat dairy products work well in a lot of recipes, I recommend sticking with the full-fat versions for cheesecake. It will help the cheesecake bake and set correctly.
• Room Temperature Is Best: While it’s not strictly necessary to use room-temp ingredients in baking, it does help the batter combine correctly and the finished product to turn out right.
• Stick With Low Speed: As with any cheesecake batter, mixing on low speed is the way to go. This prevents excess air from making its way into the filling, which can cause cracks to form in the cheesecake.

Tasty Variations

While I think this recipe is just about perfect as-is, it also works beautifully with many other textures and flavors. These are just a few of the ways you can customize your pineapple upside down cheesecake:

• Omit the Cherries: If you’re not a big fan of cherries, you can definitely leave them out of this recipe. The cheesecake will still be delicious, and gorgeous, too.
• Add Pecans: Scatter fresh pecans in and around the pineapple rings before baking, or arrange roasted pecans on top of the finished cheesecake. If you omit the cherries, you could use pecans in their place!
• Add Rum: A splash of rum or rum flavoring in the pineapple layer adds a lovely depth and fragrance.
• Add Coconut: Pineapple and coconut are a classic combo! Garnish your finished cheesecake with a generous sprinkling of dried, flaked coconut, for a beautiful tropical taste.

Storing Leftover Cheesecake

If you have leftovers, make sure to keep them at their best! Store it in an air tight container in the fridge. Leftover cheesecake will keep in the refrigerator for 2 – 3 days. 

Can I Freeze This?

Yes, you can! To freeze cheesecake, wrap it tightly in a layer of plastic wrap, and then a layer of foil. Freeze for up to 1 month. Thaw in the refrigerator before serving. You can freeze a whole cheesecake, or for convenience, freeze individually-wrapped slices.

See How to Make It

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