I have a super fun recipe for you today – Pineapple Upside Down Cupcakes Recipe. I think it is safe to say that we love cupcakes around here.

Close up of an Upside Down Pineapple Cupcake on a white plate with another cupcake behind it.

Cupcakes are easy to make and delicious too!

This is a great recipe, because you get the deliciousness of pineapple upside down cake but in the convenience of cupcakes.

They are perfect to serve on a warm summer or day, a Baby Shower brunch a Mother’s day brunch, or just because.

I mean – really, do you need a reason to make cupcakes? Especially one as delicious as this.

There are tons of kids in my house so we love making cupcakes instead of cakes because you don’t have to worry about cutting the cake correctly or anyone fighting over who’s piece is bigger than the others !

Make sure you try some of our delicious cupcakes. I know you will find more your family will love.

What are Pineapple Upside Down Cupcakes?

If you love pineapple upside cake, you are going to love these easy pineapple upside down cupcakes. They have all the flavors of the traditional cake but they are in a cupcake form!

For these pineapple upside down cupcake, we’re starting with a delicious yellow cupcake and we top each one with brown sugar, butter, pineapple and cherry!

Not only are they pretty to look at, they are packed with flavor too.

Of course, I would love to make these from scratch but I have found that a cake mix saves tons of time without taking away any of the flavor. You are going to love this easy shortcut!

A photos of the ingredients needed to make the cupcakes: Pineapples, cake mix, vegetable oil, eggs, butter, brown sugar and cherries


  • Canned Pineapples
  • Yellow Cake Mix
  • Vegetable Oil
  • Pineapple Juice
  • Eggs
  • Melted Butter
  • Brown Sugar
  • Maraschino Cherries

This is all you need to make these delicious and easy upside down pineapple cupcake recipe!

Close up image of pineapple upside cake.

How to make Pineapple Upside Down Cupcakes

  • First preheat oven to 350 degrees F and spray a muffin tin with non stick cooking spray.
  • Then remove the pineapple from the can and cut the pineapple rings into quarters.
  • Next combine the cake mix, pineapple juice, oil and eggs in a mixing bowl and beat on low until incorporated. I used a hand held mixer for this step but a stand up mixer would work great too!
  • In a separate large bowl combine the melted butter and brown sugar and stir by hand until well blended. Then spoon approximately 2 teaspoons of the brown sugar butter mixture into each cup of the muffin tin.
  • Place the pineapple chunks in a circle around bottom with a maraschino cherry in center. Then fill each cup 2/3 full with the cake batter.
  • After all the muffin tins have been assembled, bake in the preheated oven for 20-25 minutes or until toothpick inserted in center comes out clean.
  • After the cook time, leave the cooled cupcakes for at least 5 minutes in the pan.

How to get them out of the cupcake tin:

  • Then run a butter knife around edges of each cup and invert onto baking sheet to remove cupcakes.
  • The main problem you might have with these is getting the cupcakes out of your cupcake pan.
  • Some people don’t have problems, but to prevent any frustration, I highly recommend buying a 12 cup silicone muffin pan. They make baking a breeze and everything you bake in them comes out perfectly for stress free baking.
  • Allow the cupcakes to cool completely on the baking sheet lined with waxed paper (for easy clean up) before serving.
4 photos showing the process of how to make the cupcakes.  1st photo is a muffin tin with butter mixture in the bottom.  The 2nd photo is the pineapple and cherries added.  The 3rd photo is the batter poured on top.  The final photo if after the cupcakes have been baked and flipped onto a baking sheet to cool.

How to keep pineapple upside down cupcakes from getting soggy:

I have made these plenty of times and have learned to never add any extra liquid to the cake batter. Ensure that you are preparing the cake mix based on the package instructions on the back and just replace the water with pineapple juice!

Also, make sure that the pineapple is well drained before adding the pineapple to the muffin tins.

Close up image of pineapple upside cake on a cookie sheet.

How to store these cupcakes?

Once these cupcakes have cooled at room temperature, I store them in an air tight container in the refrigerator. As long as they are stored correctly, these cupcakes should last up to 5-7 days in the refrigerator.

Can these be made head of time?

I prefer these to be made the day that they are going to be served but you can definitely make them 1 day ahead of time as well.

If you make ahead of time, I recommend making them based on the recipe. Let them cool at room temperature and then store them in the refrigerator until you are ready to serve.

A top image of the cupcake showing the pineapple and cherry on top of the cupcake.

Pineapple Upside Down Cupcake Tips:

  • For the Pineapple, I like to use a pineapple slice as I find that they are easier to drain and work with. You can also use canned pineapple tidbits or crushed pineapple as well. Just make sure that either are well drained before place them in the muffin cups.
  • I use a cookie scoop to fill the tins with the cake batter. I find that this really helps speed up that process and makes sure I don’t overfill the cupcake tins. If you don’t have a cookie scoop, a ¼ cup works great for filling the muffin tins too.
  • Using a hand held mixer or stand up mixer makes making the cake batter quick and easy!
  • Don’t forget to allow them to sit for 5 minutes before attempting to remove from the pan. They will fall apart if you try to remove them right out of the oven.
Close-up of a pineapple upside cupcake on a baking sheet.

Print the recipe here:

Pineapple Upside Down Cupcakes

5 from 6 votes
You have to try these pineapple upside down cupcakes. You can the flavor of pineapple upside down cake but in the convenience of cupcakes. I know you will love them.
Prep Time 15 mins
Cook Time 25 mins
Total Time 40 mins
Servings 24
Cuisine American
Course Dessert
Calories 192
Author Eating on a Dime


  • 20 oz canned Pineapples
  • 1 box Yellow Cake Mix
  • 1/2 cup Vegetable Oil
  • 1 cup Pineapple Juice
  • 3 Eggs
  • 1/3 cup melted Butter
  • 2/3 cup Brown Sugar
  • 24 Marischino Cherries


  • Preheat oven to 350.
  • Cut pineapple rings into quarters.
  • Spray muffin pan with non stick spray.
  • Combine cake mix, oil, eggs and pineapple juice in a bowl and beat on low until incorporated.
  • In another bowl combine melted butter and brown sugar and stir until blended.
  • Spoon 2 teaspoons of butter mixture into each cup.
  • Place pineapple pieces in a circle around bottom with cherry in center.
  • Fill each cup 2/3 full with batter.
  • Bake 20-25 minutes or until toothpick inserted in center comes out clean.
  • Allow to cool in pan for 5 minutes.
  • Run a butter knife around edges of each cup and invert onto baking sheet to remove cupcakes.

Recipe Notes

This is a fun recipe, because you get the deliciousness of pineapple upside down cake but in the convenience of cupcakes.

Nutrition Facts

Calories 192kcal, Carbohydrates 28g, Protein 1g, Fat 8g, Saturated Fat 5g, Cholesterol 27mg, Sodium 189mg, Potassium 51mg, Sugar 19g, Vitamin A 125IU, Vitamin C 11.3mg, Calcium 60mg, Iron 0.7mg

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More Cupcake Recipes:

You have to try these pineapple upside down cupcakes. You can the flavor of pineapple upside down cake but in the convenience of easy cupcakes made with a cake mix. You are going to love this easy, homemade Pineapple Upside Down Cupcakes. #eatingonadime #cupcakerecipes #pineappleupsidedown #dessertrecipes
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About the Author

Hi, I’m Carrie. Welcome to Eating on a Dime!

I’m on a mission to help you cook delicious meals without busting your budget. Together we are going to cook real food… for real families.

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Recipe Rating


  1. Can’t wait to try these. But how much pineapple juice is needed? The recipe doesn’t say. Thank you ?

  2. I also want to know how much of the pineapple juice to use as it is not stated in the recipe??
    Also can these be made in cupcake holders-paper or the silicon type?
    TU, Mary

  3. Mary – I’m so sorry about that – It’s 1 cup of Pineapple Juice for this recipe. I replace the water needed for the cake mix with pineapple juice instead and it works great! I have updated the recipe on this post.

  4. 1 cup of Pineapple Juice is needed for this recipe. I use Pineapple Juice instead of the water amount listed on the cake mix. I have updated the recipe on the post. Thank you!

  5. My son-in-law LOVES pineapple upside down cake! I always make our children their favorite cake for their birthday’s. So, his birthday is Saturday & I’m going to make his this year with this recipe! Prayerfully they turn out great! Thanks for the cupcake idea for this amazing cake!

  6. 5 stars
    Love this recipe – makes for such an easier slice of pineapple upside down cake.