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!

Seriously.

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!

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!
Prep Time 20 minutes
Cook Time 35 minutes
Servings 16
Calories 405kcal

Ingredients 

  • 1 box yellow cake mix prepare box as directed using ingredients it calls for
  • 12 ounces cool whip topping thawed

Pineapple Upside Down Sauce

  • 1 cup butter
  • 2 cups brown sugar
  • 40 ounce Pineapple Chunks 2 (20 ounce cans) drain juice but reserve 5 Tablespoons of juice for the sauce
  • 3 Tablespoons cornstarch

Instructions

  • Mix as the package directs. Pour batter into a spayed cookie sheet or jelly roll pan (size is on preference) and bake at 350 degrees for 16 to 20 minutes or until cake springs back to the touch. Set aside and cool.

Pineapple Upside Down Sauce

  • In a medium sauce pan melt butter.
  • Add brown sugar. 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.
  • Cut the cooled cake into 1 inch cubes.

Trifle Assembly

  • In a trifle bowl place 1/3 of the cake on the bottom of the bowl.
  • Pour 1/3 of the cooled pineapple sauce over the top of cake.
  • Spread 1/3 of the cool whip over the top of the pineapple sauce.
  • Repeat the layers two more times.
  • Garnish with maraschino cherries.

Nutrition

Calories: 405kcal | Carbohydrates: 71g | Protein: 2g | Fat: 14g | Saturated Fat: 8g | Polyunsaturated Fat: 1g | Monounsaturated Fat: 3g | Trans Fat: 1g | Cholesterol: 34mg | Sodium: 350mg | Potassium: 166mg | Fiber: 1g | Sugar: 54g | Vitamin A: 427IU | Vitamin C: 7mg | Calcium: 129mg | Iron: 1mg
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Enjoy!

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Filed under: cake, dessert

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Comments

    1. Tara

      5

      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 question......do 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. Bonnie

      My guess is that all of the juice is drained from the 2 cans of pineapple and then 5 tablespoons are reserved from that.
      The instructions would read: In a medium saucepan, melt butter. Add brown sugar and drained pineapple *juice* (except for the reserved 5 tablespoons). Bring to a ..... Continue with instructions as written.

    3. Alana Grover

      I am halfway through this recipe and realize it is unclear. Do we only use the 5 tablespoons of juice? I see no one else had the questions answered.

    4. Chef in Training

      I am SO so so sorry for the confusion. I get so many comments and somehow missed all these. I rewrote the recipe to hope clarify any issues. The 5 Tablespoons of reserved pineapple juice mix together with the cornstarch to make a slurry to thicken it up. I am so sorry again for the poor description. Hopefully this helps clarify now :)

    5. Chef in Training

      I am SO so so sorry for the confusion. I get so many comments and somehow missed all these. I rewrote the recipe to hope clarify any issues. The 5 Tablespoons of reserved pineapple juice mix together with the cornstarch to make a slurry to thicken it up. I am so sorry again for the poor description. Hopefully this helps clarify now :)

  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?

    1. Meredith

      Based on experience (and the 16 min cook time) I figured too it had to be a jelly roll pan - which worked nicely. In paragraph 2 I think the word juice got left out of the second sentence This is how I made it and it worked great:
      2. In a medium sauce pan melt butter. Add brown sugar, and drained pineapple juice. Bring to a boil and cook for 1 minute. Add drained pineapple. In a small bowl stir the reserved 5 tbsp of 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.

    2. Chef in Training

      I am SO so so sorry for the confusion. I get so many comments and somehow missed all these. I rewrote the recipe to hope clarify any issues. The 5 Tablespoons of reserved pineapple juice mix together with the cornstarch to make a slurry to thicken it up. I am so sorry again for the poor description. Hopefully this helps clarify now :)

  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. Lori

    5

    I made this for Easter and it is amazing!!! Assembled the day before and refrigerated overnight. I was afraid the brown sugar mixture would crystallize, in the fridge, but it was perfect. Everyone loved it. The only tip I would add is the sugar/pineapple mixture takes a long time to cool so prepare for that.

  5. Tania Williams

    5

    I made this today and loved it. I did make a few changes. I added some of the leftover pineapple juice to the cake mix in place of water. Of course, it had to cook longer. I also poked holes in the cake while it was still hot and added about half a cup of cherry juice mixed with pineapple juice. I chopped some of the cherries and folded them into the Cool Whip. It turned out great.
    Also, to answer the pineapple question, I added them after I boiled the brown sugar and butter for one minute.

  6. Sue Mills

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

  7. Nicole Melanson

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

    1. Lori Jo

      1

      so, how did you translate the ambiguous recipe? When did you add the drained pineapple?

    2. Chef in Training

      I am SO so so sorry for the confusion. I get so many comments and somehow missed all these. I rewrote the recipe to hope clarify any issues. The 5 Tablespoons of reserved pineapple juice mix together with the cornstarch to make a slurry to thicken it up. I am so sorry again for the poor description. Hopefully this helps clarify now :)

  8. 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!

  9. Rachel

    Can you use fresh pineapple?

  10. Nicole

    Do you refrigerate it after making it or let it stay at room temp?

    1. Chef in Training

      cover with plastic wrap and store in fridge.

  11. 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.

    1. Pam

      I was also confused. I added drain pineapple to butter and brown sugar, boiled for a minute then added the cornstarch w/pineapple juice an boiled for 15 min

    2. Judi

      It is now May, 2022, and the pineapple question has still not been answered! Has anyone made it a certain way with no bad effects? Thank you!

    3. Chef in Training

      I am SO so so sorry for the confusion. I get so many comments and somehow missed all these. I rewrote the recipe to hope clarify any issues. The 5 Tablespoons of reserved pineapple juice mix together with the cornstarch to make a slurry to thicken it up. I am so sorry again for the poor description. Hopefully this helps clarify now :)

    4. Chef in Training

      I am SO so so sorry for the confusion. I get so many comments and somehow missed all these. I rewrote the recipe to hope clarify any issues. The 5 Tablespoons of reserved pineapple juice mix together with the cornstarch to make a slurry to thicken it up. I am so sorry again for the poor description. Hopefully this helps clarify now :)

  12. Annemarie

    I made this today......looks amazing!
    I baked the cake on a cookie sheet. I think a jelly roll pan is perfect too.
    I was reading some questions about the pineapple mixture. Here is what I did
    .melted the butter, added the brown sugar and mixed then I added the drained pineapple. Brought this to a boil then I added the reserved pineapple juice and cornstarch mixture. This mixture cooks to get thick for about 15 minutes. I stirred often. After the mixture was nice and think I transferred to another bowl to cool completely.

  13. Taren

    I have the same questions about the instructions. Could someone please respond I would really like to make this for a function. When do you add the pineapple chunks

    1. Chef in Training

      I am SO so so sorry for the confusion. I get so many comments and somehow missed all these. I rewrote the recipe to hope clarify any issues. The 5 Tablespoons of reserved pineapple juice mix together with the cornstarch to make a slurry to thicken it up. I am so sorry again for the poor description. Hopefully this helps clarify now :)

  14. Heather

    5

    I doubt it matter at which point you add the pineapple because it is cooked for 15 minutes anyway with the mixture. I added it at the beginning and it turned out great. Very delicious.

  15. Tess

    Think about it , the pineapple is always baked along with the brown sugar sauce in a regular pineapple upside down cake. So , I would add the drained pineapple in the brown sugar sauce and cook it for the one minute as instructed. I think the additional “add drained pineapple” statement was in error because you would have raw pineapple mixed in with the cooked ingredients. It sounds delicious and I can’t wait to try it.

  16. Darlene Thompson

    since we didn't get a response to the drained pineapple question, im going to experiment and put in the 2nd can of drained pineapple and see how it goes...

    1. Chef in Training

      I am SO so so sorry for the confusion. I get so many comments and somehow missed all these. I rewrote the recipe to hope clarify any issues. The 5 Tablespoons of reserved pineapple juice mix together with the cornstarch to make a slurry to thicken it up. I am so sorry again for the poor description. Hopefully this helps clarify now :)

  17. Mary

    You add the drained pineapple juice to the butter and brown sugar and boil, then add the pineapple.

    1. Chef in Training

      I am SO so so sorry for the confusion. I get so many comments and somehow missed all these. I rewrote the recipe to hope clarify any issues. The 5 Tablespoons of reserved pineapple juice mix together with the cornstarch to make a slurry to thicken it up. I am so sorry again for the poor description. Hopefully this helps clarify now :)

  18. kelly

    What size cookie sheet do you use? I have many different sizes. Thank you.

  19. Lynn

    5

    This is delicious. I added the pineapple after I cooked the brown sugar and butter together for a minute (I didn't add the drained pineapple at the same time as the brown sugar). I ended up using 20 oz of whipped topping. Fantastic dessert!

  20. Megg

    Hi, I'd love to make this but I'm a bit confused about the addition of the drained pineapple. You say to add it to the melted butter along with the brown sugar, to bring to a boil & cook for 1 minute - then to, again, add drained pineapple. Not quite sure at which point I'm supposed to add it. If you could clarify this I'd love to make it for Christmas. If I don't hear back in time - maybe for the next holiday. Thanks!

    1. Chef in Training

      I am SO so so sorry for the confusion. I get so many comments and somehow missed all these. I rewrote the recipe to hope clarify any issues. The 5 Tablespoons of reserved pineapple juice mix together with the cornstarch to make a slurry to thicken it up. I am so sorry again for the poor description. Hopefully this helps clarify now :)

    2. Megg

      5

      No worries! As I'm no novice to cooking/baking I decided to wing it & it came out fantastic. I did make homemade whipped cream to use instead of cool whip & used a little (a lot!) of extra juice cause I like things *saucy*. :-) I loved it, everyone else who tried it loved it & I will be making it again (& again). I grew up with my mom making the absolute best pineapple upside down cakes I've ever had in her cast iron pan, which I've also made - and this is (close to!) just as delicious, but SO much easier! The only thing I'll do differently the next time I make it is to scatter the cherries over the pineapple mixture layers instead of putting them on top. The cherry juice ran on the top of the whipped cream & being a bit ocd, I spent a good bit of time fixing it. lol This recipe is a keeper! Thank you for the recipe & the mom memories! :-)

  21. Jodi

    5

    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.