Pineapple Right Side Up Cupcakes

Did you know that April 20th is National Pineapple Upside Down Cake Day? I totally didn’t! The moment I found out (via a tweet or blog or something), I became mildly obsessed with the notion that I MUST make something involving pineapple, cherries, cake and brown sugar. And so I do! I find a healthy pineapple cupcake recipe on my favorite healthy eating blog,, and adapted it to be a pineapple upside down cake-esque dessert. I fed these to a bunch of college girls and they all loved them.

Pineapple Right Side Up Cupcakes

Original recipe by Skinny Taste (I made mine to be more Pineapple Upside Down Cake-ish).



  • 1 box of yellow cake mix
  • 20 oz can crushed pineapple in juice (do not drain)
  • 1/4 cup brown sugar


  • 8 oz 1/3 less fat cream cheese
  • 20 oz can of pineapple in juice, drained (squeeze really well in your hands to get out all the juice)
  • 1 1/2 cup marshmallow cream
  • maraschino cherries for garnish (optional)


Mix cake mix and 1 can of pineapple WITH the juice. I used my KitchenAid stand mixer. Use an ice cream scoop to fill lined cupcake tins about 2/3 full. Bake according to cake mix directions or until a toothpick inserted comes out clean. Set aside to allow to cool completely on cooling racks.

Drain the other can of pineapple. Like super crazy drain! I drained it in a mesh strainer and then put it in my hands, freshly washed of course, and squeezed out the excess juice. Combine cream cheese, crushed pineapple and marshmallow cream and mix until combined well. Again, used my stand mixer. Spread on completely cooled cupcakes.

For a fun garnish and to get the Pineapple Upside Down Cake Day theme across, I added maraschino cherries. I took the stems off half of the cherries and stuffed one inside each cupcake for a little filling surprise. I garnished each with a stem on cherry. On a couple that I presented to others, I dusted a little brown sugar on top to set in the purpose of the cupcake even more.

Cupcakes with no icing are 3 points each according the Weight Watchers Recipe Builder. With just icing they are 4 points each. With icing and cherries they are 5 points each. Even at their highest, they are way better than any regular cupcake a far as points values go.

Yields 24 servings. 

Pin It

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s