Pineapple Upside Down Cupcakes

Yummitty yummy yummy yum.

I think those were the exact words used to describe these cupcakes when we took them to a friend’s house for Easter.  Although I may have been the one to say it.  And it might have just been in my head.  And it might have been my fifth cupcake of the day.  But I did receive an “Oh these are delicious little treats” from everyone else at the party.

Our friends are a lot more eloquent than I am apparently.

Either way these make a delicious spring and summer treat and are surprisingly easy to make.  I like that in a recipe.

The ingredients:

Can of crushed pineapple (I ended up using two of the mid size cans), 1/2 cup of butter, 1 cup brown sugar, and a box of cake mix (plus whatever you need for the cake mix, usually some water, oil, and eggs.

Preheat the oven and mix together the cake mix according to the package directions.  Here’s a little tip: drain some of the juice from the pineapple can and use it as half of the water needed for the cake mix.  It adds some additional pineapple goodness.
In a bowl melt the butter and brown sugar, stirring well to combine.

Spray a cupcake pan with some cooking spray.  When I was making these I decided to make half of them with cupcake liners and the other half just in the pan with some cooking spray to see which ones would work the best.  While they both came out of the pan just fine the shape of the cupcakes baked without the liners was much better.   I recommend skipping the liners all together and just using cooking spray.

Pour a spoonful of the butter/brown sugar mixture into the bottom of each cupcake tin and then add a spoonful of the crushed pineapple, pressing it down into the butter/sugar mixture.

Pour the cake batter on top until the cupcake tins are 2/3 full.  Put in the oven and bake according to the cake mix directions.  After baking remove from oven and run a butter knife around the edges of each tin.   Use the same knife to level the tops (which will become the bottoms in a second) to make them flat.  Turn the pan upside down on a cooling rack, each cupcake should slide right out with the pineapple mixture now on top.

See the difference?

They taste delicious just like this or with a little bit of cream cheese frosting drizzled on top.  And you can always add a cherry on top for a more traditional pineapple-upside- down-cake-look.

This recipe makes 24 cupcakes and from start to finish took about 30 minutes to make.  No one will guess how easy they were!

Yummitty yummy yummy yum.


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11 Responses to Pineapple Upside Down Cupcakes

  1. Willa says:

    Looks so yummy!

  2. Linda says:

    These sound amazing!

  3. Michelle says:

    Wow – these look yummy, Thanks :)

  4. Lori says:

    Sounds super yummy!! Thanks for sharing!!

  5. Allison @ Room Mom 101 says:

    Hi! First of all I have to say that I discovered your site via Pinterst and I love all the wonderful gift basket ideas you have. You are so creative! I featured your drink tags on my blog (linking back to your site)so parents can get ideas for teacher appreciation. Thanks for sharing your creative ideas here!

  6. Anonymous says:

    How long do they bake? Thanks!

  7. Caroline says:

    I am making these right now! they are currently in my oven I hope they turn out okay.. They are a birthday present the mom. :)

  8. Carissa says:

    I just tried this recipe and it was a COMPLETE DISASTER! I think the technique of using pineapple rings on the bottom works so much better than with crushed. Because all that pineapple just fell off the sides once I flipped them out of the pan. Just a tip for any other readers who may have had the same issue

    • Brie @Darling Doodles says:

      Hi Carissa, I’m sorry the recipe didn’t work out for you! I wish I knew why it went wrong. We make these pretty regularly and haven’t had an issue so I don’t know how to help. Thanks for giving it a shot though and leaving your feedback!

  9. Betty819 says:

    This recipe is right up my alley..simple and delicious! My husband is diabetic and I noticed that Pillysbury is now making SF cake mixes and SF canned frosting. I have not tried them yet but if it’s easy, it would help both of us. He is such a sweets eater and after 49 years of marriage and since there are just the two of us; we tend to eat out some weeks more than we should. He can’t go into the grocery store without buying store bought pastries. I am tired of preaching to him about those sweets being dangerous to his health. His diabetic Dr. is too easy going and not strict enough on him.

    Just found your blogspot this morning via pinterest and I love what I have seen. You are very talented and creative. And one of my favorite colors is purple but I tend to like lighter shades. Guess you call them lavender or lilac.

  10. asmaa says:

    looks really yummy i”ll try them!! thanks for sharing

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