Pineapple Upside Down Cupcake

Pineapple Upside Down Cupcake is one of our family favorites.  I decided to try a cupcake version that would be a little easier to serve.  My son gave this recipe a thumbs up (his mouth was full of cake at the time so that’s pretty much all he could manage).

To keep it simple I used a boxed yellow cake mix. Of course, your favorite from scratch recipe would work just as well.

Pineapple Upside Down Cupcake

  • 1 yellow cake mix (prepared to directions)
  • or your favorite from scratch cupcake base recipe
  • 1 large can crushed pineapple (drained – set aside juice)
  • 3/4 stick of butter
  • 1 cup brown sugar

In a saucepan over low heat melt the butter and brown sugar. Add the drained pineapple and let caramelize (about 10 – 15 minutes) stirring frequently so that it doesn’t burn.

Prepare the batter and fill cupcake tins 1/2 full (if you aren’t using liners be sure and thoroughly grease the muffin pan). Be sure to leave some of the batter as you will want to go and top off each muffin later. Drain excess syrup from the caramelized pineapple and add a small teaspoon full to each muffin. “Top off” the cupcakes with the remaining batter leaving enough room for the cupcakes to rise.

Bake according to the cupcake recipe you are using.


I’m going to give you two frosting options.  The picture above is option one but personally I prefer option two.

Option 1- Regular Frosting

1 stick butter
3 1/2 cups powered sugar
Pineapple juice drained from crushed pineapple
2 Tablespoons crushed pineapple (optional)

Soften the butter, add to your mixing bowl and cream. Gradually add in powered sugar until well blended. At this point add pineapple juice to get the frosting to the desired consistency. Fold in the crushed pineapple.

To frost the cupcakes put frosting in zip top sandwich bag.  Cut corner off and pipe in a circular motion over the top of the cupcake

Option 2 – Homemade Whipped Topping

1 pint heavy cream
1 cup sugar
1/2 teaspoon of vanilla

Combine cream, sugar and vanilla with mixer until stiff.  You will want to scrape the bowl down to make sure everything is well combined.

If you go this route just make sure that you aren’t frosting until the cupcakes are ready to be eaten.  The whipped topping will not keep well on top of the cupcakes


This recipe has been featured at:

Twinkle in the Eye
House of Hepworths

Be sure and check out these sites for other great ideas.

You might also like:

How to Make Coaster Tiles
Applesauce Cupcake with Brown Sugar Frosting
Breakfast Bowls

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32 thoughts on “Pineapple Upside Down Cupcake

  1. Stopping by from Nifty Thrifty! This sounds incredible – I love pineapple upside down cake, but never make since I would eat the whole thing. I really like the idea of the cupcakes, i can eat and still keep portion control! I’m going to try this out this week. Really does sound so good! My fingers are crossed you’ll share your creative cupcakes tonight with Sunday’s Best – sharing is a good thing!

    • My daughter doesn’t like pineapple either so I just didn’t fill a couple of the cupcakes, plus when I was making the frosting I pulled a little out before I added the pineapple and juice. That way she could have plain old cupcakes while the rest of us indulged in pineapple goodness 🙂

      Thanks for stopping by!

  2. Tickled pink your shared your pineapple upside down cupcakes with us. I do have can of crushed pineapple in the pantry, I’ll let you know how they turn out! Thanks for sharing your creative inspiration with Sunday’s Best – you helped make the party a success!

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