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Pineapple Upside Down Cupcakes

When you can pick up a sweet treat and eat it with your hands you have found the pot of gold. These pineapple upside down cupcakes are delish.

There’s nothing quite like a tasty treat that is portable to make it all the more fun and exciting. These pineapple upside down cake cupcakes are easy to make and even easier to eat!

Try out this fun recipe for the summer today!

When you can pick up a sweet treat and eat it with your hands you have found the pot of gold. These pineapple upside down cupcakes are delish.

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Cupcakes are all the rage!  These baby cakes are being served everywhere. You can find them on the dessert table at family meals or even at weddings.

It doesn’t surprise me that people love cupcakes. When you can pick up a sweet treat and eat it with your hands you have found the pot of gold. 

And these pineapple upside down cupcakes are delicious. Pineapple Upside Down Cupcakes have become my husband’s new favorite dessert.

I’m a chocolate loving kind of girl, but can definitely eat my way through a few Pineapple Upside Down Cupcakes when the opportunity presents itself.

You will need a few simple ingredients to get you started:

Yellow Cake Mix (eggs, oil, water) Whatever your particular mix calls for


Brown Sugar

Crushed Pineapple

Maraschino Cherries 

Something to grease your cupcake tins with. (I use Crisco, but a good non-stick spray should work, too)

You will also need to have some wax paper on hand so you can invert the cupcakes onto the wax paper when releasing them. 

Pineapple Upside Down Cupcakes

Here are a few tips to make this recipe work better:

When mixing these cupcakes if your cake mix calls for the water you will be replacing it with the pineapple juice you drained from the can. If you don’t have enough juice just add water until you get to the right measurements.

Be sure your cupcake tins are well greased. This will prevent sticking. 

When you add the butter, brown sugar pineapple and cherry push it down with the back of a spoon so it’s an even layer. 

Put these on the middle oven rack. 

If you are using a dark pan reduce your cooking temperature by 25 degrees. 

Let the cupcakes cool for 5 mins before inverting them. 

Following those few tips will ensure that these cupcakes will be a new family favorite if you can keep them around long enough for everyone to try! 

Curious minds want to know, Do you eat the cherry on top of your pineapple upside down cake?

I do not! If it was a chocolate covered cherry I’d probably eat it. But it’s a big no on maraschino cherries for me!

If you’re interested in a savory cupcake, be sure to try out these Maple Bacon Cupcakes next!

Printable Pineapple Upside Down Cake Cupcakes Recipe:

Pineapple Upside Down Cupcakes

Pineapple Upside Down Cupcakes

Yield: 24
Prep Time: 15 minutes
Cook Time: 25 minutes
Total Time: 40 minutes

These easy pineapple upside down cake cupcakes are sure to be a hit. They're delcious, adorable, and portable!


  • 1/2 cup butter, melted
  • 1 1/2 cups brown sugar
  • 24 maraschino cherries
  • 20 ounce can crushed pineapple drained
  • 1 box of your favorite yellow cake mix
  • 3 eggs
  • 1/3 cup oil
  • 1 1/3 cup pineapple juice


  1. Move an oven rack into the middle of the oven. Preheat oven to 350 degrees F.
  2. Grease 24 muffin cups. (Try using shortening or a good non-stick spray)
  3. Line a work surface with waxed paper
  4. Spoon 1 teaspoon melted butter into the bottom of each 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 yellow cake mix as directed adding in your oil, eggs, etc.. replacing the water with pineapple juice until moistened, about 30 seconds. Turn mixer speed to medium and mix for 2 minutes.
  9. Pour cake batter into the muffin cup, filling them almost 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 wax paper to release. Serve with pineapple and cherry sides up.


The oil and eggs are listed in the ingredients because every yellow cake mix I have ever used calls for those ingredients in those measurements. You may have to adjsut the ingredients accordingly depending on the cake mix you use.

Crushed pineapple works best.

Nutrition Information
Yield 24 Serving Size 1
Amount Per Serving Calories 225Total Fat 8gSaturated Fat 3gTrans Fat 0gUnsaturated Fat 4gCholesterol 33mgSodium 202mgCarbohydrates 37gFiber 1gSugar 27gProtein 2g

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  1. These are so cute! I love anything in mini form! Thanks for sharing! #homeMattersParty

  2. Delicious looking cakes – thank you for sharing with Pin Worthy Wednesday

  3. Your cupcakes look awesome. I have made these before and really like how they turn out. I think they are classy to take to a function (or just eat) and I prefer the baby cake thing anyway. Great job

  4. Individual servings are the BEST! These look delicious. Thanks for sharing at FTAF

  5. Pinned this one – my husband’s favorite dessert!

  6. How far in advance can you make these? Is there enough juice from the crushed pineapple?

    1. Yes there is plenty of juice. I have only ever made them in the AM and served them in the PM. Thanks!

  7. When you say ‘muffin cups’ do you you mean a muffin pan or individual muffin cups without the pan? I know this is a silly question ?

    1. We used a muffin pan, but have actually had much better luck making them in a silicone muffin cup. Either works! Thanks for stopping by.

  8. sharon shafran says:

    makes my mouth water just looking at this recipe

  9. Crystal @ Zipperheadcreations.com says:

    We recently made a Pineapple Upside Down Cake for Memorial Day and it was awesome. How much cooler would it be to have in individual servings? Yummy!

  10. Now that is a cupcake I could enjoy. It looks nice and moist and tasty and no need for frosting. What a great idea they are. Thanks for bringing them to #HomeMattersParty I am going to pin them to remind me how to make them.

  11. Oh yummy! I’m going to have to make these this weekend. I have all the ingredients except the cherries. My kids are going to love these! Especially when I flip it over and there’s a cherry on the bottom!

    Thanks for sharing!

  12. I love pineapple upside down cake – these cupcakes are a great idea!

  13. Mmmm, these look amazing. I’ve been toying with my mind about making pineapple upside down cake and I think these were the deciding factor. YUM!