Easiest Pineapple Upside Down Cake Recipe

Yesterday while the girls were busy, I decided we needed something sweet to brighten up our day. It had been FOREVER since I made a pineapple upside down cake!

My mom used to make this exact recipe when I was little and it always felt so special when that warm caramel-y goodness came out of the oven.

Some of my best childhood memories are standing on a chair in our kitchen helping mom arrange those perfect pineapple rings.

Now I’m passing down those same memories to my girls.

Especially my youngest who loves being my little kitchen helper even though we always end up with sticky fingers and flour everywhere!

This recipe is so easy that even a 7 year old “helping” me it still turned out perfect. No fancy ingredients needed.

Let me show you just how simple this family favorite really is…

The Secret to Making This Look and Taste Homemade

Want to know the REAL secret to why this recipe is so easy?

I use a boxed cake mix! Yep thats right.

No shame in my game!

I just doctor up a yellow cake mix with a little vanilla and maybe some extra butter and it tastes totally homemade.

The magic happens with the brown sugar and butter in the bottom of the pan anyway.

Ingredients for Easy Pineapple Upside Down Cake

This cake is seriously the tastiest thing I’ve made in weeks (and I’ve made cheesecake and a strawberry no bake cake)!

It comes out so incredibly moist and fluffy every single time.

The caramelized brown sugar creates this rich gooey topping that soaks just a little into the cake making it absolutely perfect.

The cake part stays so light and tender that my fork just glides through it.

We barely had any leftovers because everyone kept sneaking back for “just one more small piece.”

Here’s what you’ll need:

• Yellow cake mix (vanilla works too)
• Eggs
• Oil
• Butter (the real stuff not margarine)
• Brown sugar
• Pineapple rings (canned)
• Maraschino cherries
• Vanilla extract
• Cinnamon

How to Make Pineapple Upside Down Cake

Step 1: Preheat your oven to 350 degrees.

Grab a 9×13 pan or a deep round cake pan.

I prefer using my cast iron skillet because it creates the best caramelization on the pineapples, but any pan works!

Just make sure its deep enough that the batter wont overflow.

Step 2: Melt about 1/2 cup butter in the microwave and pour it into the bottom of your pan.

Make sure the butter covers the entire bottom of the pan.

Sometimes I use the back of a spoon to spread it evenly if it doesn’t naturally coat everything.

Step 3: Sprinkle brown sugar evenly over the melted butter.

Don’t be shy with it! I use about a cup of packed brown sugar.

The more sugar, the more of that yummy caramel sauce you’ll get. Try to break up any lumps with your fingers so it melts evenly during baking.

Step 4: Arrange your pineapple rings in a pretty pattern on top of the brown sugar.

I usually fit about 7-9 rings depending on the pan size.

Don’t throw away that pineapple juice from the can! You can substitute some of the water in your cake mix with it for extra flavor.

Step 5: Place maraschino cherries in the center of each pineapple ring and any empty spaces between them.

Drain them well or they might make your cake too wet.

Sometimes I also add some chopped pecans in the spaces if we’re feeling fancy.

Step 6: In a large bowl mix together your cake mix, eggs, oil and water according to the box directions.

I usually add a splash of vanilla and a tiny bit of cinnamon too.

Don’t overmix or your cake will be tough, just stir until everything is combined and most of the lumps are gone.

The batter should be pourable but not too thin.

Step 7: Pour the cake batter carefully over the pineapple arrangement.

You can use a spatula to gently guide the batter into all the corners without messing up your pineapples.

Step 8: Bake for about 35-40 minutes or until a toothpick comes out clean from the center.

The top should be golden brown.

Every oven is different so start checking at 30 minutes. The cake should spring back when you lightly touch the center.

Step 9: Let the cake cool for just 5 minutes (set a timer or you might forget like I did last time while breaking up a fight between the kids).

This cooling step is super important, too long and the caramel will harden and stick to the pan, too short and the cake might fall apart when you flip it.

Step 10: Place your serving plate upside down on top of the cake pan, then carefully flip the whole thing over so the pineapple side is now on top.

The pan might still be hot so use oven mitts!

This is the moment of truth that always makes me nervous no matter how many times I’ve made this cake.

Step 11: Slowly remove the cake pan and prepare for the oohs and aahs when everyone sees those beautiful caramelized pineapples!

If any pineapples or cherries stick to the pan just carefully place them back where they belong on the cake.

That warm butter-brown sugar mixture will be bubbling around the edges, this is liquid gold!

Serve it warm with vanilla ice cream!

This cake also tastes great the next day if you have any leftovers which rarely happens in our house. Just cover it with plastic wrap once it’s completely cool.

The Pineapple Upside Down Cake Recipe

Here’s everything you’ll need to make this super yummy cake that my family goes crazy for.

Serve it warm or at room temperature. Its even better with a scoop of vanilla ice cream on top!

Pineapple Cake Worth Making

There you have it!

If your looking for a dessert that will impress without the stress, this pineapple upside down cake is your answer.

The caramelized sweetness paired with tangy pineapple is just perfect for family gatherings.

Sometimes the old recipes are still the best ones.

Give it a try this weekend and I promise you won’t regret it.

Make sure to follow me on Pinterest for more yummy food ideas!