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
Comments & Reviews
Mayra says
Im making IT right now
Hope I can Do it!!!!????
Dana DeVolk says
Yes, you can!
Pd says
Can I use a box cake mix?
Dana DeVolk says
Yes, you can!
Kristen says
Do you know if you can do half the amount for the cheesecake so it is a thinner later in the middle?
Dana DeVolk says
I have never tried, but I think it would work. I’m not sure how long it would need to bake for though. If you do this, please let us know how it comes out!
Valerie says
I just finished the cakes. I made the cheese portion 2 days ago and
Refrigerated it. The top was nice golden brown and it was set.
My question is the cheesecake part is soft and not solid like a NY cheese. Is that the way it should look? I followed all instructions to the letter.
Brittney Causey says
I made this cake last night! I had to come write a review because I love baking, but I haven’t had all the experience in the world because I’m only 20, haha. So with that being said I’ve never made a pineapple upside down cake OR a cheesecake. But it came out so well. Yes it tests your patience but if you follow the instructions you’ll be happy you did. I’ve always been one to rush putting icing on a cake and then it melts. So I was very impressed that the cheesecake turned out well for my first time. The cakes are dense, but I think it’s better that way because I used canned pineapple and it’s almost like a buttery, caramelized pinapple sweetness absorbed through the cakes and they were definitely not dry. They also were NOT soggy and falling apart in any way or even crumby. When I assembled the layers I just looked at it in awe because I was almost certain I would’ve messed it up. So Thank you for this recipe! I posted it on my Facebook and everyone seemed jealous 🙂
Dana DeVolk says
Thank you so much for your thorough review Brittney! I agree, the cakes are a bit dense but they need to be in this instance. I’m so glad you liked the recipe!!
Sarina says
I cannot find the recipe itself…i can see the comments and the pictures but no recipe. Please help! I would love to make this cake for my dads birthday…this was his favorite flavor at Cheesecake factory! Thank you!
Dana DeVolk says
The recipe is at the bottom of the post right before the comments. It is blocked off in a printable recipe card. Thanks!
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.
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 🙂
Barbara Brizendine says
Maybe the size of the springform pan. Recipe said to use a 9″. Instant Pot size springform is a lot smaller.
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 !!
Jen Ruby says
Can I do this in 8inch pans, if so what would be the baking times?
Dana DeVolk says
That is the cooling down process. I will update the recipe, you are welcome to skip this one 🙂