Healthy Pineapple Upside Down Cake

This healthy pineapple upside-down cake is made using oat flour for a heart-healthy version of this potluck favorite!

This recipe comes to you courtesy of a reader request! A few weeks back, I received the following email from a reader: 

Hello! I love your recipes… especially your oat flour breads & cakes! They’re delicious !! I wondered if you could figure out how to make a healthy oat flour pineapple upside down cake It’s my favorite, and I’m afraid to try to figure it out myself! Have you ever tried it ?? Thanks! – Nerissa

If you’ve never heard of pineapple upside-down cake, it was a dish very popular in the seventies and eighties but remains an American classic today. It gets its name because the topping is cooked on the bottom, and then the cake is flipped once it cools so that the bottom becomes the top or upside-down. Or, as my three-year-old would say, upside over. 

 I’ll be honest, pineapple upside-down cake has always been one that intimidated me, but I LOVE reader requests, so I figured I’d take a stab at it.  Well, I stabbed this one around five times!  It’s an easy cake to make but challenging to develop a recipe for because you have to account for the pineapple topping weighing the cake down.  Compound that with the fact that oat flour is a very dense flour, I knew it might take a few tries.  

We loved the result of this moist and fruity cake!  It is a bit denser and oatmeal-like than my other oat flour cakes, but that’s relative because pineapple upside-down cake is generally heavier and more moister than other cakes. So, I might call it pineapple upside-down oatmeal on social, so I don’t get yelled at, haha (I’ll probably still get yelled at.) But, here will call it a healthy pineapple upside-down cake that is gluten-free, can be made dairy-free, and is of bright flavors pineapple and cherry flavors and sweet cake in every bite. I hope y’all enjoy this one!  

How to Make Pineapple Upside Down Cake

I know, a ton of photos here.  This recipe isn’t complicated, though. It just happens to require a lot of bowls.  Similar to my banana oat flour cake. 

You’ll start by pouring butter or vegan butter into the pan, brushing the pan so that all sides are coated, then sprinkling in some brown sugar.  I chose to mix my brown sugar in and did not substitute it with coconut sugar here.  I felt coconut sugar would not give me the caramelized glaze I was looking for.  

You’ll dry your fruit and then arrange it in the pan however you would like.  In the video and final photos, you’ll notice I used a whole pineapple ring in the center, which caused the pineapple half-rings to droop over the side. This was gorgeous, in my opinion! Or you can use a half ring in the center (as shown below), and then you can arrange the other half-rings to not droop over the edge of the cake.  Either way is fine! 

After this, you’ll need THREE bowls.  Two medium bowls and one large one.  You’ll add your flour mixture to one of the medium bowls and your milk mixture to another.  

In the final large bowl, you’ll cream together your butter and sugar. I used coconut sugar for a less refined sugar option, but you can also use plain old white sugar (more swaps and substitutions below.) And then add your eggs to the butter-sugar mixture and beat again. 

Next, you’ll alternate beating in the flour and milk mixture.  I used an electric beater since I already had it out. You can also fold it with a spatula.  We don’t have delicate gluten fibers to protect with oat flour, so it isn’t a big deal which you chose. 

Pour the finished batter over the pineapple cherry topping and bake! 

See, not hard, just a lot of bowls and steps. 

Swaps and Substitutions

8- inch cake pan: This recipe was developed in an 8-inch cake pan.  If you use a 9-inch, it will be very thin, so I wouldn’t recommend it.  I also recommend a metal pan. It will be less heavy and easier to flip than a glass pan.  

Pineapples – use canned, dry thoroughly, and don’t substitute fresh pineapple.  Make sure you get pineapples in JUICE, not syrup.  The pineapples in syrup will be too heavy, and you need the juice later on. 

Maraschino cherries – optional, but not.  Dry thoroughly. 

Butter –  feel free to substitute vegan butter here. The Trader Joe’s one is my favorite.  I wouldn’t sub coconut oil, palm oil, or any other oil. It just won’t be the same taste-wise.  

Sugar – the topping calls for brown sugar, you can try coconut sugar, but it may not come out as caramelized.  For the sugar in the cake, you can use white sugar or coconut sugar, or any other dry sweetener, with no liquid substitutions such as honey or maple syrup.  

Oat Flour – this recipe was developed using oat flour, do not substitute.  If you’d like to use another type of flour, I suggest trying to find another recipe using that specific flour.  Or send me a request!

Baking Powder/Baking Soda/ Sea Salt / Vanilla – do not omit or sub. 

Almond milk – sub any non-dairy milk from a carton or water, do not use canned coconut milk or dairy milk as it may be too heavy for the oat flour. 

Pineapple Juice – Since you already bought your canned pineapples in juice, you probably don’t need to substitute it.  But, if you for some reason poured out the juice and are in a bind, you could use orange juice.  

Yogurt – plain yogurt, ideally not greek yogurt, but it could work.  For dairy-free, plain cashew milk yogurt will work.  

Softened Butter – has to be softened to cream with the sugar, I know, it’s obnoxious, but it’s the way of the baking world.  

You could try substituting this with flax eggs, but I would expect the final product to be a bit heavier.  I’d add a little more baking powder if this is the case.  Or maybe try an egg substitute like Bob’s Red Mill instead of flax eggs. 

Storing and Freezing Instructions

To store: As moist as this cake is, do not be fooled. This cake will dry out!  Make sure you cover it with saran wrap once it’s cool and place it in the refrigerator within 12 hours.  In an ideal world, you eat it within 24 hours and store the leftovers in an airtight container for up to 3 days.  

To freeze?:  My initial reaction is that this is not the type of cake that would be good frozen.  Most cakes aren’t good frozen, but with the extra liquid content, this recipe contains and the canned fruit on top. So I would say probably skip freezing.  If you want to try it, wrap it tightly in saran wrap, freeze for up to 3 months, and defrost under refrigeration.  

More Oat Flour Cake & Dessert Recipes:

•  Banana Oat Flour Cake
•  Oat Flour Carrot Cake
•  27+ Oat Flour Dessert Recipes

Tag me if you make this cake! I love to see what you guys make! You can tag me on Insta @hungryhobbyRD and Facebook @hungryhobby!