Pineapple Upside Down Cupcakes

When I was a little girl, my mom would make pineapple upside down cupcakes for me and my sisters.

We all loved them! Even now, as an adult, I can’t resist their deliciousness.

One of our favorite desserts now in single serving sizes. This is the same great taste as the full size dessert, only smaller and cuter versions.

These are great if you want something special over the Holidays, or for birthdays.

Let us know what you think in the comments below. Happy baking!

Scroll to bottom for printable recipe card.

Why we love this recipe

The sweet and sticky pineapple, the moist and fluffy cake, and the rich and creamy frosting all come together to create a truly heavenly treat. Plus, they’re just so darn cute!

What is Pineapple Upside Down Cake?

This is a classic dessert that has a layer of pineapple, a cherry and brown sugar. The cake is usually a yellow, pineapple or butter flavored cake. The cake is usually inverted so that the brown sugar, pineapple and cherry are on the top of the cake.

Should I use fresh or canned pineapple?

That is a tough choice. Fresh is always the best no matter how you look at it. However, it is more expensive. Canned pineapple will not taste as fresh as fresh pineapple. Ultimately, the choice is up to you.

Can I use a yellow cake mix instead of pineapple?

Pineapple cake can be difficult to find. If you want to go ahead and use the yellow cake mix. Instead of the entire amount of water, add in the juice from the canned pineapple(if you use canned). This will add to the flavor of the cake.

How do you add flavor to pineapple upside down cupcakes?

You could add crushed pineapple to the cake batter, you could add pineapple extract. As mentioned earlier, use the juice from the canned pineapple in place of some of the water for the cake. You could also make a pineapple glaze to cover the cupcakes.

Are they hard to remove from the muffin tin?

It can be somewhat tricky to remove the pineapple upside down cupcakes from the muffin tins. I have found the best way to do that is to place a 9×13 cake pan over the muffin pan. This should be so that the cake pan is covering the muffin tin. Once the pineapple upside down cupcakes are completely cooled, keep the pan over the top and while holding both the pan and the muffin tins, quickly flip the set over. Gently lift the muffin pan off.You will then be able to use a spatula to move the cupcake.

How do I know if the cupcakes are done?

To test the cupcakes, use a toothpick inserted in the center. Not all the way through, just three-fourths of the way. If the toothpick comes out clean, they are done.

Ingredients:

• Sweet cream butter
• Light brown sugar
• Maraschino cherries
• Crushed pineapple
• Pineapple cake mix
• Eggs
• Pineapple juice
• Canola oil
• Powdered sugar

Directions:

Step 1. Position the oven rack in the middle of the oven.

Step 2. Preheat oven to 350 degrees.

Step 3. Prep muffin cups with nonstick baking spray.

Step 4. Add one teaspoon of melted butter in each of the muffin cups,

Step 5. Top the melted butter with one tablespoon of light brown sugar.

Step 6. Position one maraschino cherry in the center of the light brown sugar in each of the muffin cups.

Step 7. Use a tablespoon measuring spoon to measure out the crushed pineapple. (heaping tablespoon)

Step 8. With the back of a spoon push down the crushed pineapple into the maraschino cherry/ brown sugar layer. Set aside.

Step 9. Add the pineapple cake mix to a mixer bowl. Mix in the eggs, pineapple juice, and oil with an electric mixer set on low until the cake mix is just moistened. (30 seconds)

Step 10. Increase the mixing speed to medium, mixing for 2 minutes.

Step 11. Scoop the prepared cake batter into each of the muffin wells. Fill just below the top of the muffin well. (Do not overfill.)

Step 12. Bake at 350 degrees for 20 minutes.

Step 13. Check to make sure the cupcakes are fully baked by inserting a toothpick in the center of the cupcake. If the toothpick comes out clean the cupcake is baked.

Step 14. Set the cupcakes on the counter to cool for about 5 minutes.

Step 15. Flip the baked cupcakes over on a cooling rack. (The cherry should be on the top of the cupcake.)

Pineapple Upside Down Cupcakes

Prep Time: 20 minutes minutes

Cook Time: 25 minutes minutes

Total Time: 45 minutes minutes

Pineapple upside down cupcakes are a delicious twist on the classic pineapple upside down cake. These cupcakes are made with a moist and fluffy pineapple cake base, topped with a rich and sticky pineapple glaze.

5 from 1 vote

Review Recipe

Ingredients 

• ½ C sweet cream butter, melted
• 1 ½ C light brown sugar
• 24 maraschino cherries
• 1 can crushed pineapple, 20 oz
• 1 package, 18.25 oz pineapple cake mix
• 3 large eggs
• 1 ½ C pineapple juice
• ½ C canola oil
• 1 Tbsp powdered sugar, garnish

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Instructions

• Position the oven rack in the middle of the oven.
• Preheat oven to 350 degrees.
• Prep muffin cups with nonstick baking spray.
• Add one teaspoon of melted butter in each of the muffin cups,
• Top the melted butter with one tablespoon of light brown sugar.
• Position one maraschino cherry in the center of the light brown sugar in each
  of the muffin cups.
• Use a tablespoon measuring spoon to measure out the crushed pineapple. (Heaping
  tablespoon)
• With the back of a spoon push down the crushed pineapple into the maraschino
  cherry/ brown sugar layer.
• Set aside.
• Add the pineapple cake mix to a mixer bowl. Mix in the eggs, pineapple juice,
  and oil with an electric mixer set on low until the cake mix is just moistened.
  (30 seconds)
• Increase the mixing speed to medium, mixing for 2 minutes.
• Scoop the prepared cake batter into each of the muffin wells. Fill just below
  the top of the muffin well. (Do not overfill.)
• Bake at 350 degrees for 20 minutes.
• Check to make sure the cupcakes are fully baked by inserting a toothpick in the
  center of the cupcake. If the toothpick comes out clean the cupcake is baked.
• Set the cupcakes on the counter to cool for about 5 minutes.
• Flip the baked cupcakes over on a cooling rack. (The cherry should be on the
  top of the cupcake.)
• Enjoy!

Author: Laura

THANKS FOR PINING!

How do I keep the cupcakes from getting soggy?

The pineapple must be drained well. If there is liquid still with the pineapple, the cupcakes will be soggy.

Do the cupcakes need to be refrigerated?

These cupcakes do not need to be refrigerated. They can be stored in an airtight container on the counter for up to 3 days. Of course, they will stay fresh longer, if they are kept in the refrigerator.

Can I freeze Pineapple upside down cupcakes?

These cupcakes can be frozen. Be sure they are wrapped tightly and in an airtight container to keep them fresh. They can be frozen for 2 months. Thaw at room temperature before serving.

Can I make these cupcakes ahead of time?

It is often better if they are made a day or two in advance. They need to be wrapped well to avoid drying out.

How long should you wait before flipping the cupcakes?

To flip them out of the muffin tin, they should be completely cool. Then they are ready to be flipped. Placing a flat tray or cake pan upside down on the muffin tin, is the best method I have found to flip the cupcakes.

How long do Pineapple upside down cupcakes last?

These will last for two days at room temperature, up to a week in the refrigerator. Be sure to keep the cupcakes wrapped to prevent drying out.

More Cupcakes I Love

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Lemon Blueberry Cupcakes – Refreshing, delicious, and unforgettable!