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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??

 

If you like this recipe, check out these others:

How to make Pineapple Upside Down Cheesecake

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4.90 from 154 votes

Pineapple Upside Down Cheesecake

Author Dana at ThisSillyGirlsLife.com
Prep: 40 minutes
Cook: 2 hours
Cooling time 5 hours
Total: 7 hours 40 minutes
Pineapple Upside Down Cheesecake, two layers of buttery pineapple upside-down cake stuffed with pineapple cheesecake, just like The Cheesecake Factory… but homemade! 
Servings 18 servings

Ingredients
  

Pineapple Cheesecake

Pineapple Upside-Down Cake Topping

Pineapple Upside-Down Cake Batter

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

Calories: 587kcal | Carbohydrates: 78g | Protein: 6g | Fat: 28g | Saturated Fat: 16g | Cholesterol: 128mg | Sodium: 278mg | Potassium: 209mg | Sugar: 58g | Vitamin A: 965IU | Vitamin C: 1.3mg | Calcium: 121mg | Iron: 1.8mg
Nutrition Disclaimer
Course Dessert
Cuisine American

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4.90 from 154 votes (134 ratings without comment)

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66 Comments

  1. 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.

  2. 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?

  3. 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?

  4. You place the pineapple in the pan, pour the batter on top, then bake

  5. 2 stars
    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.

  6. 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?

  7. 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.

  8. You’re right, I’m not sure why I put 12, I’m fixing it, thanks!

  9. 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.

  10. 3 stars
    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.

  11. Wow, a lot of negativity in the comments. I’m a fairly seasoned baker, followed this recipe exactly. It came out beautifully!! My grown daughters and family loved it and have requested several times since I first made it .

  12. Frederick Osborne says:

    5 stars
    that looks great how much $$$

  13. 8″ pans of the same height as 9″ pans have meaningfully less volume, ~21% or close to 1/5 less. The same amount of batter in the 8″ pan would be deeper than in the 9″, ~27% or just over 1/4 deeper.

    It’s often good to have the baking pans only 2/3 full or so, to allow room for rising. Using the same amount of batter in the 8″ pan would significantly cut into that margin, and it would require longer baking time. (The 9″ pan has more surface area exposed, versus the 8″, and the thicker layer of batter means it takes longer to get the center done.)

    Probably best to reduce the amount of batter – around 80% or 4/5 as much would give you a similar batter thickness in the 8″ pans. The overall smaller size, with no change in batter thickness would then mean slightly less baking time for the same amount of doneness.

  14. Looking at the calorie amount listed, which usually is per serving. Seriously, 587,000 per serving????

  15. Christine says:

    5 stars
    This is the second time I have made this and find it very satisfying to see how it comes out in the end. AND it’s delicious!!❤️

  16. 5 stars
    I’ve made this 2 times before for family. They really liked it. Sorry to see the negative comments. I’m in the process of assembling #3 today for Easter. I know growing up that Grandma’s UDC was pretty dense so don’t care for a fluffy UDC.

  17. This is nothing like the one from Cheesecake Factory!

  18. 5 stars
    This turned out great. The cake IS huge, though, so…. hopefully you have people to share it with!

  19. should the cheesecake be assembled with the pineapple upside down cake is still war

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