Pineapple Upside Down Cheesecake, two layers of buttery pineapple upside-down cake stuffed with pineapple cheesecake, just like The Cheesecake Factory… but homemade!
Who knew your two favorite desserts could get any better, pineapple upside down cheesecake for the win.
Pineapple Upside Down Cheesecake
Oooooh boy… you know we love our cheesecakes. I have posted many a cheesecake recipe. But, normally it’s all about what Jeremy likes *eye roll*
…. but yesterday it was my birthday so it has been all about what I likes. So, I wanted a massive dessert for my birthday… is that a crime?!
My favorite cheesecake from The Cheesecake Factory of all time is their Pineapple Upside-Down Cheesecake. It’s a lightly flavored pineapple cheesecake layered between two buttery pineapple upside-down cakes.
It’s Heaven, basically.
So, for my epic birthday cake this year, I made this bad baby! It’s everything I hoped for! And then some. Cheesecake Factory cheesecakes are big… but this… this thing is ginormous!
This recipe, like my last cheesecake cake Strawberry Shortcake Cheesecake, takes a little planning ahead.
I suggest making the cheesecake the day ahead and letting it get nice and cold in the fridge overnight. BUT, the pineapple upside-down cakes should be made the day of for a nice presentation.
You can still eat it for days and days after but that first day it will look the best.
The recipe for the cheesecake is adapted from Allrecipes.com and for the pineapple upside-down cakes from Sally’s Baking Addiction (I’m obsessed with her, I know.)
This recipe contains affiliate links
Tools Needed to make Pineapple Upside Down Cake Cheesecake:
I have to be honest, I always get nervous after typing up a recipe like this. It looks like it’s totally complicated and will take forever but in reality, it’s not that bad.
Sure, this recipe probably isn’t for a complete beginner but just break it down into steps. Just look at the cheesecake recipe, then the topping, then the batter. See, not that bad.
I’m also being sensible with the portion sizes, believe me, a small slice of this goes a long way!!
Yummm, excuse me while I wipe the drool off my keyboard. This is one heck of a cake!!
I truly hope you liked today’s recipe! What is your favorite Cheesecake Factory cheesecake flavor??
How to make Pineapple Upside Down Cheesecake
Pineapple Upside Down Cheesecake
Ingredients
Pineapple Cheesecake
- 4 8 oz packages cream cheese room temp
- 1 1/2 Cups granulated sugar
- 3/4 Cup milk
- 4 eggs
- 1 Cup sour cream
- 1 Tablespoon vanilla bean paste or extract
- 1/4 Cup all purpose flour
- 1/3 Cup pineapple juice
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
- 3 1/3 Cup all purpose flour sifted
- 1 teaspoon baking powder
- 1/2 teaspoon baking soda
- 1 teaspoon salt
- 1 Cup unsalted butter melted
- 1 1/2 Cup light brown sugar packed
- 1/2 Cup granulated sugar
- 2 eggs
- 1/2 Cup sour cream
- 1 Cup milk
- 1/2 Cup pineapple juice
- 2 Tablespoon vanilla bean paste or extract
Instructions
Pineapple Cheesecake
- Preheat oven to 350 degrees. Grease a 9-inch springform pan. Cream the cream cheese with the sugar until smooth in a large bowl. Mix in the milk fully then add in one egg at a time and mix. Add in the remaining ingredients and mix until smooth with no lumps.
- Pour into the pan and bake for 1 hour, the center will be slightly jiggly. Shut off oven and let cool down in the oven for 5 hours. Top with plastic wrap and place in fridge overnight to get cold.
Pineapple Upside-Down Cake
- Start with the topping by dividing the melted butter equally between two 9 inch cake pans. Sprinkle 1/2 Cup of the brown sugar into each pan. Arrange the pineapple slices and cherries as pictured, set aside.
- Preparing and cooking the cake: Preheat oven to 350 degrees. In a large bowl, add in the sifted flour, baking powder, baking soda, and salt, whisk to combine.
- In a medium-sized bowl, add in the 1 Cup melted butter, brown sugar, and granulated sugar. Whisk to combine, getting all the brown sugar lumps broken up. Whisk in the eggs, sour cream, milk, pineapple juice and vanilla until combined.
- Add the wet mixture to the dry mixtures and mix until combined, with no dry spots or lumps.
- Evenly divide the batter between the two pans, about 2/3 of the way full, do not overfill!
- Line oven with foil or two cookie sheets, cakes may bubble over some. Bake for 48-53 minutes, covering loosely with foil at the 20-minute mark to avoid burning. Cakes are down when a toothpick inserted in the middle comes out clean.
- Place cakes on a wired rack to cool for 10 minutes.
Pineapple Upside-Down Cheesecake Assembly
- Invert cakes, one onto a flat surface like a cutting board and the other on the plate you will be presenting on.
- Take out the pineapple cheesecake. Trim top of the cheesecake if it is not even. Take it out of the pan and lift it off the bottom carefully, you may need to use a tool like a frosting spatula to help. Place on top of the first cake layer. Trim the sides of the cheesecake with a knife if necessary. Place the second layer of cake on top. Serve as is or with whipped cream, enjoy!!
Nutrition
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Marisa says
I wonder if I messed something up.. I never made a Cheesecake before, and really don’t make cakes for that matter.. I just finished the Cheesecake batter but when I poured it into the 9″ spring form pan its literally all the way to the top of the pan.. So then I thought, maybe cheesecake shrinks because it’s cheese.. Now I’m watching it ooze out of the pan in the oven lol.. Did I mess something up? Or does this make more better than needed?.. My lack of inexperience is showing lol
Dana DeVolk says
Errrrr… that definitely shouldn’t happen. The cheesecake layer isn’t that thick. Did you somehow double the recipe on accident?!
Rhi says
I just had this same problem and I followed the recipe exactly. It’s got 12 minutes left and is just about to overflow…
Dana DeVolk says
I honestly don’t know why there would be an issue. Did you happen to add the cheesecake batter on top of one of the pineapple cake batters and baked it that way? Everything should be baked separately.
Barbara Brizendine says
Maybe the size of the springform pan. Recipe said to use a 9″. Instant Pot size springform is a lot smaller.
Rhi says
Nope, I did just the cheesecake. It didn’t actually overflow, just came close. And when I took it out of the oven 5 hours later it did shrink back down a little bit but it’s still a lot thicker than your pictures, so I’m not sure. At least it didn’t overflow though 🙂
Charles Mccarthy says
Total cooking time is 7 hrs. 40 mins not 2 hrs 40 mins. Read your own instructions ! Not willing to leave any product in oven for 5 hrs. Cooked or raw !!
Dana DeVolk says
That is the cooling down process. I will update the recipe, you are welcome to skip this one 🙂
Jen Ruby says
Can I do this in 8inch pans, if so what would be the baking times?
Occasional Baker says
I made this for a fund raiser, people were intrigued but intimidated by the size of it, This makes a fairly large slice of cake..I thought it was very good but I think it(the cheesecake) needs just a little more pineapple flavor… Loved it and was fairly simple to make.
Tammy says
It says to bake cheesecake for 1 hour then shut oven off leave in cake let cool for 5 hours in the oven. Is that right leave in cooling oven for 5 hours?
Dana DeVolk says
Yes, that’s right
Kim says
When I saw this recipe, I wanted to try it immediately. I guess I misread the instructions about the cheesecake. I thought it read bake for an hour and then turn the oven off and cool an hour then 5 hours in the refrigerator. Next time I will add more pineapple flavor in the cheesecake. Also, I agree the pineapple upside down cakes were too dense so I will be adjusting that part of the recipe. But, wtbs, my family enjoyed the cake. I will be making it again, just with some adjustments.
Deanna says
hi!! Maybe I’m too new at this but when you bake the pineapple cakes and I supposed to place the pineapple on the bottom of the pan and then pour the batter in? Or am I supposed to bake the cakes first then place the pineapple rings on top and bake for a little more?
Dana DeVolk says
You place the pineapple in the pan, pour the batter on top, then bake
Jessica says
So far I’m not happy with this recipe. I’m a skilled baker and have made plenty of cakes and cheesecakes. The cheesecake rises way too much and is too soft. The cakes are too dense and cook times for both took much longer than in the recipe directions. I would make this recipe again but with using cheesecake recipes I’ve done in the past and my favorite 8-yolk cake recipe.
Barb says
The recipe calls for only 12 pineapple slices, but the picture shows 7 on the top and both cake layers are to be the same. That would be 14 slices?
Dana DeVolk says
You’re right, I’m not sure why I put 12, I’m fixing it, thanks!
Lori says
Obviously you have never made a cheesecake before. That is a pretty standard practice for cheesecake. You probably should skip this one.
Planned on making this for Easter this year and just decided I was too tired. My Husband said “I’ll do it!” so him and my 26 year old son spent a few hours in the kitchen and made this. It was excellent! This will be a go to for sure.
They are not bakers, but they nailed this. It is a huge cake so we shared some with friends and they loved it too.
Terrie says
I’d have to agree with most of the comments about the cheesecake being very thick. There was also way too much cake batter. I hade a cake order for a pineapple upside down cheesecake. I tested this recipe and added an extra egg to the batter. I filled the two 9 in cake pans 2/3 full and had a ton of batter left over. The cheesecake batter almost went to the top of my 9 in spring form pan. Once done cooking and cooling it did shrink but it was too thick. The cake was really good the cheesecake I’ve made better. When I remade the recipe for my order I made 3 cake layers using 9 in pans and 2 cheesecake layers with 9 in pans. It’s a monsterous cake. Not sure how this recipe makes the cake you are showing. Mine is twice the size. No I didn’t double anything. Followed the recipe but added an extra egg since I read that the cake was too dense.