Skip to main content

Double Layer Pineapple Upside Down Cake

Looking for a show-stopping dessert that's both delicious and nostalgic? This Double Layer Pineapple Upside Down Cake is one of my most requested bakes, a sweet, moist cake topped with caramelized pineapple rings and cherries.

Double layer pineapple upside down cake with caramelized pineapple and cherries

When I baked from home to earn extra income, this cake quickly became a customer favorite — and it's still one of the most-loved recipes I make today. 

What you'll need:

  • 1 box yellow or pineapple cake mix (15.75 oz), plus the ingredients listed to make the cake (i.e. eggs, oil)

  • Pineapple rings

  • Maraschino cherries

  • Crushed pineapple

  • Brown sugar

  • Butter

(Full ingredient measurements and instructions are below.)


Ingredients for Double Layer Pineapple Upside Down Cake, cake mix, pineapple, maraschino cherries

Tips for Baking Success

1. Adjust for New Cake Mix Sizes

Cake mix boxes have shrunk over the years. If you're using a 15.75 oz mix, bake the cakes in 8-inch round cake pans for the best results.


Want to use 9-inch cake pans? No problem! Use a cake mix upsizer to make up the difference and avoid thin layers that are hard to flip and stack.

Crushed pineapple and brown sugar in round cake panPineapple rings, maraschino cherries and brown sugar in a round cake pan.

2. Mind Your Layers

Keep track of which pan has the pineapple rings and cherries and which one only has crushed pineapple. This way, you can flip and stack the layers in the correct order without a mess.

Baked cakes cooling in pans on wire rack.

3. Watch the Temperature

If you're using a dark-colored pan, reduce the oven temperature by 25°F to prevent over-browning.

 

Cake layer turned out onto rackCake layer turned out onto rack

4. Timing Is Key

After baking, let the cakes cool in their pans on a wire rack for about 30 minutes, no longer!
If they cool completely, they'll stick, and you'll risk losing that gorgeous, caramelized topping when you flip them out. 

Pro Tip: If the crushed pineapple layer sticks, you can gently lift it off with a spatula and reassemble it on top.

 

Double layer pineapple upside down cake on serving plate

 

How to Assemble Your Cake

  1. Turn out the layer with the crushed pineapple onto your serving plate first.

  2. Then carefully flip the second cake layer with the pineapple rings and cherries on top of it.

 

Slice of Double Layer Pineapple Upside Down Cake on blue and white plate with a fork.

FAQ

Can I make this pineapple upside down cake ahead of time?
Yes. This cake can be baked a day in advance and stored covered in the refrigerator. Let it come to room temperature before serving.

How should leftovers be stored?
Cover tightly and refrigerate for up to 4 days. Reheat slices briefly for best texture.

Can I use homemade cake batter instead of a mix?
Yes. A homemade yellow cake batter works well as long as the volume matches a standard box mix.


Close up image of a bite of Double Layer Pineapple Upside Down Cake on a blue and white plate.

I hope you’ll give this Double Layer Pineapple Upside Down Cake a try! It’s such a fun twist on a classic dessert and always a hit wherever I bring it. If you bake it, I’d love to hear how it turned out, leave a comment, tag me in a photo, or leave a star rating on the recipe card. I love seeing your creations!

If you enjoy pineapple desserts, try my Pineapple Upside Down Muffins for an individual-size version. Looking for a breakfast spin? My Overnight Pineapple Upside Down Oats use the same flavors in a no-bake format.

 

Double Layer Pineapple Upside Down Cake

Double Layer Pineapple Upside Down Cake
Author: Jolene's Recipe Journal

Ingredients

  • 4 Tablespoons butter
  • 1/2 cup packed brown sugar (light or dark)
  • 2 Tablespoons shredded coconut, optional
  • 20 ounce can pineapple slices
  • 13 maraschino cherries, no stems
  • 20 ounce can crushed pineapple with juice
  • 1 package yellow or pineapple cake mix (15.75 ounces), plus ingredients to make cake
  • Cake mix upsizer, if making 9" cakes

Instructions

  1. Preheat oven to 350 degrees F. Melt butter and coat the bottoms of 2 - 9-inch round cake pans. Drain and reserve the juice from both cans of pineapple.
  2. Sprinkle the bottom of each pan with 1/4 cup of brown sugar. Sprinkle coconut in one pan, if desired. Lay pineapple rings in a single layer on top of coconut. Place a cherry in the center of each ring. In the other pan, spread the drained crushed pineapple.
  3. Prepare the cake batter with an electric mixer, substituting the reserved pineapple juice for the water called for on the package, until smooth and fully combined. Divide the cake batter between the 2 pans. Remember which pan has the pineapple rings in it. 
  4. Bake for 40 to 50 minutes, or until a toothpick inserted into cake comes out clean. Cool in pans on a wire rack for 30 minutes.
  5. Turn the layer with the crushed pineapple out onto the serving dish, then gently turn the other layer on top

Notes

Source: Allrecipes, Submitted by Donna

pineapple, cherries, upside down
Cake, Desserts
American


Comments

  1. Your cake is so beautiful! I'll have to hunt down that cake mix!

    ReplyDelete
  2. I love pineapple upside down cake! This is a great way to make it even easier with a mix!

    ReplyDelete

Post a Comment

Popular posts from this blog

Easy Stuffed Waffles with Sweet and Savory Fillings

Stuffed waffles are a fun twist on the classic waffle—crispy on the outside and packed with tasty fillings inside. I recently got a stuffed waffle maker, and I’m loving how it turns waffles into little pockets of deliciousness! The best part? You don’t need a strict recipe because this is a perfect “clean out the fridge” meal. Grab whatever leftovers or fillings you have on hand, stuff ’em inside, and waffle away! Here’s what I tried this time, but feel free to get creative and make it your own.

Strawberry Pizzelles

Pizzelles are one of my favorite childhood cookies and I'm constantly looking for ways to put a new spin on them.  Since one of my favorite summer fruits is strawberries, I swapped out the vanilla in the original recipe with strawberry extract.