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.

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 (ie eggs, oil)

• Pineapple rings

• Maraschino cherries

• Crushed pineapple

• Brown sugar

• Butter

(Full ingredient measurements and instructions are below.)

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 pans for the best results.

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

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.

3. Watch the Temperature

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

 

4. Timing Is Key

After baking, let the cakes cool in their pans 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.

 

 

How to Assemble Your Cake

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

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

 

 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 — feel free to leave a comment, tag me in a photo, or leave a star rating on the recipe card. I love seeing your creations!

 

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 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. Mix the cake as directed on package, but substitute reserved pineapple juice in place of water. Divide 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 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

Recommended Products

Wilton Diamond-Infused Non-Stick Navy Blue Round Baking Pan, 9-inch

Other recipes you may enjoy:

Pineapple Upside Down Muffins #MuffinMonday

Pineapple Upside Down Overnight Oats

pineapple, cherries, upside down

Cake, Desserts

American