Pineapple Upside Down Cake Trifle

Pineapple Upside Down Cake is one of my favorite desserts.

I love how each and every bite is infused with a brown sugar pineapple sauce and how it melts in my mouth!

The flavor is magical.

This trifle takes every component that makes that cake special and transforms it into a delicious, beautiful, new dessert.

Pineapple Upside Down Cake Trifle... This recipe is INCREDIBLE! Layers of cake, glazed pineapple mixture and cream... it is sure to be a hit wherever you serve it!

If you are looking for an incredible dessert to serve your company… look no further!


This trifle is a show stopper. Anyone who loves Pineapple Upside Down Cake is going to go CRAZY for this trifle!

Pineapple Upside Down Cake Trifle... This recipe is INCREDIBLE! Layers of cake, glazed pineapple mixture and cream... it is sure to be a hit wherever you serve it!

5.0 from 2 reviews
Pineapple Upside Down Cake Trifle
This recipe is INCREDIBLE! Layers of cake, glazed pineapple mixture and cream... it is sure to be a hit wherever you serve it!
  • 1 yellow cake, and ingredients it calls for
  • 12 ounces cool whip
Pineapple upside down sauce
  • 1 cup butter
  • 2 cups brown sugar
  • (2) 20 ounce cans pineapple chunks, drained. (reserve 5 Tablespoon of juice)
  • 3 Tablespoons cornstarch
  • 5 Tablespoons reserved pineapple juice
  1. Mix as the package directs. Pour batter into a spayed cookie sheet and bake at 350 degrees for 16 to 20 minutes or until cake springs back to the touch. Set aside and cool.
  2. In a medium sauce pan melt butter. Add brown sugar, and drained pineapple. Bring to a boil and cook for 1 minute. Add drained pineapple. In a small bowl stir reserved pineapple juice with cornstarch. Slowly pour into the butter, pineapple mixture. Return to a boil and cook for about 15 minutes until mixture begins to thicken. Cool completely.
  3. Cut the cooled cake into 1 inch cubes.
Trifle Assembly
  1. In a trifle bowl place ⅓ of the cake on the bottom of the bowl.
  2. Pour ⅓ of the cooled pineapple sauce over the top of cake.
  3. Spread ⅓ of the cool whip over the top of the pineapple sauce.
  4. Repeat the layers two more times.
  5. Garnish with maraschino cherries.


If you make this recipe, snap a photo and hashtag it #chefintraining and/or #chefintrainingblog. I would love to see how these recipes take shape in your kitchens.

Filed under: cake, dessert

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    1. Tara


      I read the ingredients,then the instructions I looked back at the ingredients because I saw 2 cans of pineapples. To the melted butter I added the brown sugar and 1 can of drained pineapples and brought to a boil then I added the 2nd can of drained pineapples and went forward with the pineapple-cornstarch and return to a boil.

  1. Mary

    Wow! One you add the pineapple to the pan before or after it comes to a boil? Thanks for sharing.

    1. Nina

      My question too! The instructions are unclear. Can't wait to make this!

  2. Suzanne Tuck

    I'm a little confused.
    1) Is a "sprayed cookie sheet" the same as a jellyroll pan? My cookie sheets are not rimmed.
    2) You are adding the drained pineapple twice. Once boiling it with the butter and brown sugar for 1 minute. And then adding it AFTER you have boiled the butter, brown sugar and drained pineapple. When is the drained pineapple added?

  3. Tasbih @ Cleobuttera

    Mmmmmm...this sounds and looks absolutely delicious! I love a deconstructed dessert, and no offense to upside-down pineapple cakes, but this one looks even better. This is a summer must-make. Pinned!

  4. Sue Mills

    When do you add the drained pinapple as the recipe states it twice. After or with the butter and brown sugar?

  5. Nicole Melanson

    I made this for a potluck pool party! It was a hit! Everyone wants the recipe!

  6. Roz

    Wow, wow, wow! This one satisfied all my cravings in one! Made it for xmas, added in a layer of custard and added passionfruit and chocolate chips on top - it all disappeared in one sitting between 3 adults! Making it again for New Year this time with pics! Thanks!

  7. Liz Melendez

    I wish someone would correct this recipe. Answer the previous questions. I have same questions, as to when to add pineapple? The recipe is confusing. I would love to make this.

  8. Jodi


    This turned out amazing. I can see where this is utterly confusing for people, though.
    Here's what I did. I didn't quite follow the instructions and it was fab and people at a party literally RAVED about it. I also bought a giant jar of maraschino cherries.
    1. Bake the cake in a jelly roll pan. Doctor it up as you see fit. (use milk instead of water, butter instead of oil, etc.).
    2. Melt the butter in a saucepan. Add the brown sugar. Boil for a minute to get rid of the brown sugar granules. Add all BUT 5 Tbsp of the pineapple juice. (In hindsight, I'd save out more than 5TB; I'd save 7TB; see below.). Stir in until well incorporated. Gently boil some more to add the slurry (see below)..
    3) While that's cooking make a slurry of the 5TB of reserved Pineapple Juice + Cornstarch. Add it to the boiling caramel in the saucepan stirring like crazy. (it wasn't enough imho because I want my caramel sauce thick like a good thick gravy (!) so I had to add another slurry of 2 TB of cornstarch + 3 TB of water - this is why I say to save aside more pineapple juice for this purpose - add more cornstarch to it, too)
    4) pull it off the boil and cool for a while (freezer it on a platter to make it cool quicker - it just needs to be cool-ish - it can still be a teeny tiny bit warm)
    5) Whip up a qt of whipping cream (cool whip is full of chemicals: gross). Put in a lot of powdered sugar (to taste), a full tsp or so of vanilla and a full (one) TB of instant vanilla pudding mix so it sets and doesn't go runny in a few hours. If you're good, put it in a piping bag w/a 1M tip.
    6) layer the trifle. Cake/Pineapple bits/Sauce/Whipping cream/a few cherries/ - do it again. Finish with piped whipping cream (it's impressive) and dot with cherries.

    Hope this helps.