Pineapple Upside Down Cake

Pineapple Upside Down Cake

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Welcome to the August Pinterest Challenge Blog Hop, hosted by My Pinterventures. The purpose of this Pinterest Challenge is to motivate all the participants of this hop (and you too) to not just pin, but to make it happen! This month, I chose to bake Pineapple Upside Down Cake topped with Dole Whip inspired by this pin

Dole Whip Topped Pineapple Upside Down Cake. Image property of Disney Parks Blog
Image property of Disney Parks Blog.

Pineapple Upside Down Cake Step By Step

First, prepare all ingredients. Gather ingredients to prepare the cake per instructions on the box. 

Drain the can of pineapple, reserving the juice.

Spoon one tablespoon of brown sugar into each ramekin. Top that with one tablespoon of the drained crushed pineapple. 

Add one half of a maraschino cherry to each ramekin in the center. Top with batter, making sure each ramekin has an equal amount of cake batter. 

Bake for 27 to 30 minutes. Cool inside the ramekins on a cooling rack. When cooled, using a knife, cut around the outside of each ramekin and invert onto a plate. When ready to serve, scoop pineapple sherbet onto the plate and enjoy! 

Pineapple Upside Down Cake Recipe

Yield: 10 servings

Pineapple Upside Down Cake

Pineapple Upside Down Cake

Pineapple Upside Down Cake topped with Pineapple Sherbet inspired by Walt Disney World's Dole Whip Topped Pineapple Upside Down Cake.

Prep Time 10 minutes
Cook Time 17 minutes
Total Time 27 minutes


  • 1 box yellow cake mix
  • 20 oz. can crushed pineapple
  • 10 tbsp. brown sugar
  • eggs and oil per box instructions
  • 5 maraschino cherries


  1. Grease 10 ramekins.
  2. Drain crushed pineapple, reserving the juice.
  3. Prepare cake mix according to box directions substituting the pineapple juice for the water.
  4. Spoon 1 tbsp. brown sugar into each ramekin. Spread evenly using a spoon.
  5. Spoon 1 tbsp. crushed pineapple into each ramekin and spread evenly using a spoon.
  6. Cut maraschino cherries in half and place one half into each ramekin.
  7. Add remaining crushed pineapple to the cake batter and mix to incorporate.
  8. Spoon cake batter into the 10 ramekins making sure they are all equally full.
  9. Bake at 350 degrees for 17 minutes or until golden and cake tester comes out clean.
  10. Cool completely.
  11. Run knife around outside edge and release cake from ramekins.
  12. Place on a plate and top with Pineapple Sherbet.
  13. Serve immediately.

Did you make this recipe?

Please leave a comment on the blog or share a photo on Instagram

Pin for later!

Pineapple Upside Down Cake
Pineapple Upside Down Cake
Pinterest Challenge Blog Hop
Pinterest Challenge Blog Hop

Come see all the other projects posted as part of this months Pinterest Challenge. If you would like to join next months #pinterestchallenge, click here to sign-up ⇒ September Pinterest Challenge.

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17 thoughts on “Pineapple Upside Down Cake”

  1. That looks so delicious! I LOVE pineapple upside down cake and yet I have NEVER tried making it myself. I really must get on that. Pinned.

  2. I’m not sure why we don’t make Pineapple Upside down cake more often because it is so easy. I have never made the individual one’s but now I plan to try! YUM!

  3. Love that these are individual size cakes. Perfect for a potluck or gathering. You know…I have never tried this before! They looks super delicious. Pinned

  4. I read a book series once with the main character being a Stefanie Plum. Her favorite cake was pineapple upside down and I told myself one day I will do the research, find a good recipe and give it a go. Probably you can guess, that I never followed up on that vow. Now I don’t have to research anymore and can start right with the baking process. Thank you so much for this. Pinning as it really looks delicious!

  5. I haven’t had upside pineapple cake in ages. I like that these are individual so it’s set portion control 🙂 Pinned.

  6. This is my favorite cake. Love that you’ve put them in ramekins. It makes for a pretty presentation.

  7. halfpintpartydesign

    I haven’t eaten a pineapple upside-down cake since my grandmother passed away. Looks like it’s time to try it again. I’m not sure my kids have ever even eaten it. The pineapple sherbet (or Dole Whip) is a fabulous way to top it off! Pinning for later.

  8. What an absolute classic, my nan used to make this all the time but always made a big cake. I like the individual portion idea, it makes it a little bit fancier.

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