Meet the Individual Pineapple Upside Down Cheesecake, you guys. There’s a lot of goodness packed into them. Not only do you get pineapple cheesecake (yay) but you also get to eat it all by yourself and they’re gluten-free.

I learned a couple of things making these, and I’ll pass along tips so you don’t have to make any mistakes. Get ready to be in pineapple, gluten-free cheesecake heaven!

For more cheesecake resources and recipes, please check out my Cheesecake Recipes page.

an individual pineapple upside down cheesecake with a ring of pineapple on top and a cherry in the center

Pineapple Upside Down Cake

Pineapple Upside Down Cake is one of my beloved childhood desserts. Mom could whip one up very simply.

Usually a two-egg yellow cake, but with pineapple juice in place of the milk in the recipe. A bed of brown sugar with rings of pineapple nestled in along with a neon red cherry in the center of each one.

It was easy to portion and serve–everyone got a square with a circle of pineapple in it.

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I love the pineapple/brown sugar/cake combo so much, I made it into a pineapple upside down pound cake and even into a pina colada ice cream cake with sauteed pineapple.

If you’re a fan of the combination too, be sure to check those guys out!

overhead shot of an individual pineapple cheesecake with a pineapple ring and a cherry on top

How to Make a Cheesecake Gluten Free

Some cheesecake recipes call for flour in the batter, and you can substitute cornstarch with no problem.

Cheesecake batters that don’t call for flour are most likely naturally gluten free if you are careful with sourcing.

So the issue with cheesecake and gluten is usually the crust.

Most cheesecake recipes call for a graham cracker crust (that’s my favorite, anyway).

Rather than going with a gluten-free graham cracker crust, crumb crust, or even a pastry crust made with gluten-free flour, I made rounds of coconut macaroons.

They’re naturally gluten-free (as long as all the ingredients are carefully sourced) and go so well with pineapple. I used the same recipe to make the cookies for my pina colada buttermilk sherbet ice cream sandwiches.

Other Gluten Free Cheesecake Crust Ideas

Aside from making a macaroon crust, you can also consider using

  • Finely chopped toasted nuts and a touch of sugar (choose the nut based on what flavor your cheesecake will be)
  • Use almond meal (which is basically super finely chopped nuts)
  • Use a mixture of gluten free oatmeal, chopped nuts, a little butter, and sugar.
  • Lose the nuts and use all gluten-free oatmeal, along with some sugar, cinnamon and butter. Whir everything up in a food processor, press into your pan, then bake until golden brown before adding your filling.

Aren’t Those Pineapple Rings Hard to Cut Through?

Yes. Yes they are.

You can do it with a serrated knife, but nobody wants to fuss with that when trying to eat a dessert, so follow the recipe and use crushed pineapple or chop up your own fresh pineapple.

I admit I used whole rings because I knew they’d look nice in the photos. While rings are great on cake, the cheesecake really isn’t sturdy enough to keep from SMOOSHING when you try to cut through the pineapple.

What Are the Components of Pineapple Upside Down Cheesecake?

There are three basic components of these little cheesecakes:

  • Macaroon crust
  • Pineapple/Brown Sugar Topping (which starts on the bottom)
  • Cheesecake Mixture

Make the Macaroon Crust First

You can bake the mixture in a sheet pan and then use a cutter to cut individual crusts, but that will leave some waste (or snacks, depending on how you look at it.

What I did was to choose the graduated cutter that was just about the same diameter as my ramekins, and pack the “cookie dough” into it. That way I could make as many crusts exactly the size I needed with no excess macaroon bits lying around.

Make the Topping Second

While the macaroons are baking, add your filling to each ramekin.

The filling is just an easy mixture of

  • dark brown sugar
  • a pinch of salt
  • rum (optional)
  • crushed pineapple
  • maraschino cherries, blueberries or other fruit of your choice (also optional)

Mix the sugar salt and rum together. Then add a equal amount to each of your ramekins. Then add the fruit in an even layer. Done!

Make the Cheesecake Mixture Last

NOTE: The recipe is written to make 4 individual cheesecakes. You can scale the recipe up to make more.

The batter is pretty standard with cream cheese, sugar, salt, some lemon zest and lemon juice, an egg, and a bit of pineapple juice.

How to Make This a Full-Size Pineapple Cheesecake

Multiply the filling ingredient amounts by 3 for a thinner cheesecake (given an 8″ cheesecake pan) or by 4 for a thicker cheesecake.

You may add a couple of tablespoons of cornstarch to make sure the liquid in the egg white, lemon juice and pineapple juice doesn’t weep.

As for the crust, you can quadruple the ingredient amounts in the recipe or use store bought coconut macaroons (making sure they’re gluten free) and whir them up in your food processor.

Then just press them into your springform. Done!

For specific amounts and a beautiful swirled Passover cheesecake check out this Gluten-Free Macaroon Crust for Cheesecake from Bunsen Burner Bakery. She suggests 10 oz of baked macaroons, or about 16.

2 individual mini cheesecakes on white plates on an orange striped background
Much like making flan or creme caramel, the brown sugar mixture will act as a sauce for your mini cheesecakes. With pineapple upside down cake, the sugar syrup soaks into the top of the cake. The cheesecake batter doesn’t soak up liquid in the same way, so expect some brown sugar caramel sauce on your plates.

I really hope you love these little gluten free pineapple cheesecake guys! If you make them, please share a photo with me, either in the PCO Facebook Group or on instagram by tagging @onlinepastrychef and using hashtag #pcorecipe. Thanks, and enjoy!

Gluten-Free Mini Pineapple Upside Down Cheesecakes

Jennifer Field
The amounts I'm giving make enough for 4 3oz cheesecake plus crust and pineapple topping. Feel free to scale up as needed, and if you want to make a full sized cheesecake, triple or even quadruple the filling ingredients.
NOTE: All ounce meaurements are by weight. Please buy a kitchen scale.
5 from 3 votes
Tried this recipe?Please give it a star rating!
Prep Time 20 minutes
Cook Time 1 hour
Chill Time 4 hours
Total Time 5 hours 20 minutes
Servings 4
Calories 765 kcal


For the Crust

  • 3.5 oz sweetened flaked coconut
  • 2.4 oz sweetened condensed milk (scant 1/4 cup) (not evaporated milk)
  • ¼ teaspoon vanilla extract
  • pinch of kosher salt
  • 1 egg white (you'll only be using 1/2 of this amount, but it's silly to try to beat 1/2 an egg white)

For the Pineapple Topping

  • 6 Tablespoons dark brown sugar , packed firmly (you can also use light brown)
  • teaspoon kosher salt
  • 8 Tablespoons crushed pineapple , drained well
  • 4 maraschino cherries , a couple of blueberries per ramekin or fruit of choice

For the Cheesecake Filling

  • 1 8 oz block cream cheese at room temperature
  • 2.5 oz granulated sugar (use between 2-3 oz sugar, to taste. My sweet spot is 2.5 oz)
  • teaspoon kosher salt
  • zest of 1/4 lemon
  • 1 large egg at room temperature
  • 1 Tablespoon freshly squeezed lemon juice
  • 1 Tablespoon pineapple juice (from the can)


For the Crust

  • Stir the coconut, sweetened condensed milk, salt and vanilla together until well combined.
  • Whip the egg white to stiff peaks. Take 1/2 and thoroughly fold into the coconut mixture.
  • Use a cutter that is the same size (or a tiny bit smaller than) the opening of your ramekins to make your individual crusts.
  • On a parchment- or Silpat-lined cookie sheet, press about 2 Tablespoons of the macaroon mixture into the cookie cutter. You want a crust that is about 1/4" thick. Remove the cutter and continue making individual crusts. I ended up with five, so one for each of the minis and one for me to enjoy as a cookie. Perfect!
  • Bake at 325F for 18-20 minutes or until lightly golden brown on the tops and deeply golden brown on the bottoms.
  • Reduce the oven temperature to 300F.
  • Let cool on the sheet for five minutes and then remove to racks to cool completely.

For the Pineapple Topping

  • Mix the brown sugar together with the salt making sure it's evenly distributed.
  • Place 1 1/2 Tablespoons (packed) of the sugar mixture evenly in the bottom of each ramekin.
  • Top that with a maraschino cherry (well-drained) or whatever fruit you're using in the center of each ramekin.
  • Carefully press 2 Tablespoons of crushed pineapple evenly over the sugar and other fruit.
  • Set aside.

For the Cheesecake Filling

  • Beat the cream cheese on low speed until smooth and creamy, scraping the bowl as necessary.
  • Add the sugar, salt and lemon zest and beat until thoroughly combined and smooth. Again, scrape the bowl as necessary.
  • Mix in the egg on low speed followed by the juices, scraping bowl as necessary to thoroughly and evenly incorporate the juice.
  • Spoon 1/4 of the mixture into each ramekin.
  • Bring about 2 cups of water to a boil.
  • Place the four ramekins in a cake pan or other baking dish large enough to hold them with at least 1/2" between each and between the sides of the pan and the ramekins.
  • Put the pan holding the ramekins on the middle rack of the oven and then carefully pour in the boiling water to a depth of about 1".
  • Bake the cheesecakes for about 40 minutes or until the internal temperature of the cheesecake is 155F. (Check at about 30 minutes and go from there).
  • Remove each ramekin from the pan of water and let cool on a rack for 30 minutes. Leave the pan of water in the oven so you're not sloshing boiling water all over the place. You can pour out the water once it has cooled off.
  • Refrigerate until chilled.

To Serve

  • Run a thin knife around the inside of each ramekin.
  • Place a coconut crust on top of the cheesecake, bottom side up, and place a serving plate on top of the whole thing.
  • Flip everything over and shake a bit to release the cake onto the plate.
  • Enjoy

Did You Make Any Changes?


Please bake these in a water bath. It keeps the heat in the oven moist and even so your cheesecake will come out smooth and creamy.
To make a full-size cheesecake, triple all ingredients (or quadruple for a thicker cheesecake) and bake in an 8" or 9" cheesecake pan.


Serving: 1gCalories: 765kcalCarbohydrates: 121gProtein: 9gFat: 30gSaturated Fat: 20gPolyunsaturated Fat: 8gCholesterol: 112mgSodium: 486mgFiber: 4gSugar: 112g
Keyword cheesecake, gluten free cheesecake, pineapple cheesecake
Did you make this recipe?Please tell us what you loved!

Thanks for spending some time with me today!

Have a lovely day, and do make some pineapple upside down cheesecake at your earliest convenience.

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  1. This is simply stunning, my friend! Beautiful and all elegant! Not our mom’s anything! I love how you made it individual which is so much nicer to serve but really isn’t it just perfect with the pineapple rounds? Kudos to you, you talented pastry chef, you.

  2. FABULOUS recipe 🙂

    I am pretty sure a serrated knife applied to the pineapple would cut through ok.
    they look fantastic with the slice on top!!

    Love your work.

    1. Oh yes, a serrated knife works great–it’s what I used to cut a not-too-messy bite. I just don’t think most folks are willing to take a serrated knife to a mini dessert! Seems rather barbaric. lol I do agree they are pretty with a whole slice, so it’s a trade off. =)

      Thanks, Viviane. xo

  3. 5 stars
    OML Jennie, you’ve done it again. This looks fabulous and the recipe is making my tastebuds do the tropical hula. Going to have to try it. Thanks for sharing!

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