Pineapple Upside Down Cupcakes

Pineapple Upside Down Cupcakes

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"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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45 m servings 236 cals
Serving size has been adjusted!

Original recipe yields 24 servings



  • Calories:
  • 236 kcal
  • 12%
  • Fat:
  • 9 g
  • 14%
  • Carbs:
  • 38.6g
  • 12%
  • Protein:
  • 1.5 g
  • 3%
  • Cholesterol:
  • 33 mg
  • 11%
  • Sodium:
  • 174 mg
  • 7%

Based on a 2,000 calorie diet

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Nutritional Information

1 Serving
Servings Per Recipe:
Amount Per Serving
  • * Percent Daily Values are based on a 2,000 calorie diet. Your daily values may be higher or lower depending on your calorie needs.
  • ** Nutrient information is not available for all ingredients. Amount is based on available nutrient data.
  • (-) Information is not currently available for this nutrient. If you are following a medically restrictive diet, please consult your doctor or registered dietitian before preparing this recipe for personal consumption.

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  • Prep

  • Cook

  • Ready In

  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.


  1. 73 Ratings

Most helpful positive review

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). ...

Most helpful critical review

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.

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). ...

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 ...

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!!

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 ...

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.

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 cookin...

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 eac...

My party starts in an hour. Made a practice batch last weekend and I ate them all... so I am not worried :)

I used fresh cherry halves, pineapple canned in light syrup, and lemon cake mix to which I added a lemons worth of lemon zest and the same of juice along with the pineapple water - from the can...

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