Pineapple Upside Down Cupcakes Recipe -
Pineapple Upside Down Cupcakes Recipe
  • READY IN 45 mins

Pineapple Upside Down Cupcakes

Recipe by  

"Love to make these little guys for family gatherings or just as treats for home to pack into lunches. Easy recipe to make. Adaptations can be made to make this completely from scratch. This is just a yummy simplified version!"

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Ingredients Edit and Save

Original recipe makes 2 dozen cupcakes Change Servings
  • PREP

    20 mins
  • COOK

    20 mins

    45 mins


  1. Move an oven rack into the middle of the oven. Preheat oven to 350 degrees F (175 degrees C).
  2. Spray 24 muffin cups with cooking spray.
  3. Line a work surface with waxed paper.
  4. Spoon 1 teaspoon melted butter into the bottom of each sprayed muffin cup.
  5. Spoon 1 tablespoon brown sugar in each muffin cup.
  6. Press a maraschino cherry into the center of the brown sugar in each muffin cup.
  7. Spoon a heaping tablespoon of crushed pineapple over the cherry and compact it with the back of a spoon into an even layer.
  8. Mix pineapple cake mix, eggs, pineapple juice, and vegetable oil in a large bowl with electric mixer on low speed until moistened, about 30 seconds. Turn mixer speed to medium and mix for 2 minutes.
  9. Pour pineapple cake batter into the muffin cups, filling them to the top; do not overfill.
  10. Bake in the preheated oven until a toothpick inserted into the center of a cupcake comes out clean, about 20 minutes.
  11. Allow cupcakes to cool at least 5 minutes before inverting muffin cups onto the waxed paper to release. Serve with pineapple and cherry sides up. Sprinkle cupcakes lightly with confectioners' sugar.
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Reviews More Reviews

Most Helpful Positive Review
Jun 26, 2012

I've been making this basic recipe for years with a couple differences: I used a yellow cake mix with the juice from the pineapple in place of the water (add water to the juice if necessary). I've used pineapple tidbits and rings cut up to fit instead of the crushed pineapple. Crushed pineapple can sometimes make the cake under it too mushy sometimes. Instead of putting the batter directly into the muffin pan, I used paper liners which is so much easier for lunches and serving at picnics. It's a surprise when they take the paper off to eat it! It's basically sweet enough for me to eat like this but occasionaly I've dusted powdered sugar on top of the cupcakes after slightly cooled. Oh, and if you're a coconut lover, add a little to the brown sugar before laying in the pineapple and cherries. This is a great recipe anyway you make it!

Most Helpful Critical Review
Apr 01, 2012

I actually made these the other day my kids said it tatses better when i make a homemade batter than with the duncan pineapple supreme.

Apr 02, 2012

Loved these! Of course baking from scratch is always nice, but this is a great way to make a yummy finger food snack without the extra work. To me adding the pineapple juice to the Duncan Hines cake mix gave it a real extra flavor boost (thanks for the tip!) I don't understand people who rate recipes down for using a mix aid, IF YOU DON'T LIKE MIX THEN DON'T MAKE THE RECIPE.

Mar 30, 2012

love these lil guys! its def more effort to do so many individual cakes but as far as presentation they're well worth it, make a cute idea for partys!!

Apr 05, 2015

I am a scatch baker as well, but we all need a short cut now and then. Made these for Easter today, along with a turkey, ham, ETC. Made 3 desserts and this one came out of the oven just in time to be served warm! Can you say Yummy!!! And pretty :) Thank you. Update: had so many requests for this again, did it today for Easter. Used a yellow cake mix (all I had) and a real pineapple that I had that was over ripe. Awesome!! Cleaned pineapple, put slices in a gallon Ziploc and squeezed them into mush. Put in a mesh strainer and pressed the juice out as much as possible, ended up with well over 2 cups. Used juice and pineapple as instructed. Came out perfect!! 13 ppl for Dinner 0 cakes left!

Jun 24, 2012

Oh these came out wonderfully. I used my larger muffin pans to make single serving cakes so there was more pineapple at the top of the cakes. I would recommend this recipe to all.

Jan 03, 2013

I don't know why I never thought to make little individual cakes like this before! I made my own cake from scratch but followed this recipe for the instructions with glaze, assembly, and cooking time. Delicious! Each little cupcake had just the right amount of caramel glaze and the little tid-bits of pineapple were so much easier to eat than the big rings in the traditional recipe. This on is a keeper! The kids had so much fun helping with this too. (I discovered after that the kids used 1 T. of melted butter in each muffin cup not 1 t. maybe that's why it was so good. :o)

Aug 03, 2012

This was very easy and very moist and delicious.We don't like the cherries, so I did not use those and I used about 1 1/2 tsp of butter in each dish and a heaping Tbsp of Dark Brown Sugar in each. I also used Pineapple Tidbits instead of crushed pineapple. I only had just over 1 cup of pineapple juice, so I added 1/3 cup of water. Definitely a must make if you like Pineapple Upside Down Cake.


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  • Calories
  • 236 kcal
  • 12%
  • Carbohydrates
  • 38.6 g
  • 12%
  • Cholesterol
  • 33 mg
  • 11%
  • Fat
  • 9 g
  • 14%
  • Fiber
  • 0.3 g
  • 1%
  • Protein
  • 1.5 g
  • 3%
  • Sodium
  • 174 mg
  • 7%

* Percent Daily Values are based on a 2,000 calorie diet.

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