Upside Down Pineapple Cupcakes

Upside Down Pineapple Cupcakes All the taste of Summer in one flavor filled bite! Taking a classic and making it new. Don't let a summer bbq pass without making these!

If you follow me on Twitter then you have been reading all my teasers about these cupcakes.  Well the waiting is over and they have arrived!!! All in their finest. I may be a bit biased as they have Plaid cupcake papers, but I think these are some fine looking pastries! Cupcakes are an all time favorite.  So when you think of creating something new and fun, traditional cupcakes might not come to mind.  I can tell you though these are no traditional cupcakes you see before you.  These cupcakes are all ready for summer!

Upside Down Pineapple Cupcakes All the taste of Summer in one flavor filled bite! Taking a classic and making it new. Don't let a summer bbq pass without making these!

I don’t know about you but I think these cupcakes are just about the most amazing morsels of all the summertime flavor favorites.  Everyone has a grandmother that makes Upside Down Pineapple Cakes.  They are dripping in brown sugar and pineapple wonderfulness.  All those wonderful memories are captured in this cupcake.  Dense sweet cake topped with pineapple buttercream and pineapple chunks cooked in a brown sugar butter glaze, all topped with that beauty of a Cherry!

Upside Down Pineapple Cupcakes All the taste of Summer in one flavor filled bite! Taking a classic and making it new. Don't let a summer bbq pass without making these!

Although this is not a sponsored post I do have to give a shout out to my friends at Dole Foods!  They had one of the best booths at BlogHer Food and I have to admit I went back more than once for Chocolate covered frozen bananas!!! Since they were so sweet and had such a nice booth I made sure to purchase Dole Pineapple Chunks.  {The Tid-bits were not available in my store.}  They truly are a superior fruit company and using quality ingredients is very important to me here at the P and P Kitchen.

Upside Down Pineapple Cupcakes All the taste of Summer in one flavor filled bite! Taking a classic and making it new. Don't let a summer bbq pass without making these!

These cupcakes are very easy to make and they have a really great “Wow!” factor if you need a fun dessert to show off with.  Throw a Luau style party if you have to, just to make these cupcakes.  I am really really happy with the results! Whenever I am developing a new recipe I always have my fingers and toes crossed hoping that they will be a success. And I can proudly say that these are fabulous!  The frosting and the pineapple glaze are really the showstoppers of these cupcakes.  Brown Sugar, butter, pineapple…… totally in love!

Upside Down Pineapple Cupcakes All the taste of Summer in one flavor filled bite! Taking a classic and making it new. Don't let a summer bbq pass without making these!

So run out to the store and Pick up some Dole Pineapple and get to baking! You will have an amazing crowd pleasing cupcake at your hands!

Upside Down Pineapple Cupcakes

Upside Down Pineapple Cupcakes


  • For the cupcakes
  • 1 20oz can of pineapple chunks and reserved juice
  • 1 box mix of yellow cake
  • 1/3 cup oil
  • 1/4 cup pineapple juice
  • 3/4 cup water
  • 2 eggs
  • 3 tbs brown sugar
  • for the frosting
  • 4 cups powdered sugar
  • 1 cup (2 sticks) Butter
  • 2 tbsp pineapple juice
  • 1 tsp vanilla
  • for the glaze
  • 3 tbsp butter
  • 1/4 cup brown sugar packed
  • 3 tbsp pineapple juice
  • 1/2 of the can of pineapple chunks {I snacked on the other half}
  • maraschino cherries well drained for garnish


  • Cupcakes:
  • preheat oven to 350
  • line 18 cupcake liners in muffin tin
  • in a mixing bowl combine all the ingredients for the cupcakes except the brown sugar and mix
  • add the brown sugar and swirl through the batter making rings
  • fill each cupcake liner 2/3 full
  • bake for 20 min
  • let cool completely before frosting
  • Frosting:
  • in a mixer with the paddle attachment
  • cream the sticks of butter and powdered sugar
  • add the pineapple juice and vanilla
  • add more pineapple juice if needed for consistency
  • beat for 5-10 min for completely smooth frosting
  • Pipe or spread on cooled cupcakes
  • Glaze:
  • in a saucepan melt the butter and brown sugar
  • add the pineapple juice and fruit chunks
  • cook over medium heat for 5-7 min until the sugar starts to caramelize and the pineapples get a nice golden color
  • let cool completely {Do Not Put in fridge to speed up cooling this will cause the butter to solidify again}
  • place completely room temp pineapples on each cupcake and drizzle some of the glaze on each
  • top with a cherry
  • Enjoy!

Here are some other really fun Summer treats!

Pina Colada Pie in a Jar

Pina Colada Pie in a Jar

Amaretto Fluff Dip

Amaretto Fluff Dip


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I have 32 lovely thoughts, I would love to hear yours.

  1. Jocelyne Santos says:

    I’m looking to make these very soon for a Chinese New Year Party.
    Pineapple cake is huge for Chinese New Year, so I though these would be perfect!
    I’m looking over the ingredients and should the 120oz canned pineapple chunks actually be 20oz can?

    Looking forward to your response!

    BTW – these look absolutely gorgeous!! Can’t wait to make them!

  2. Lauren says:

    Do these last a while with the cherry and pineapple on it? I am making them tonight for family coming to visit me and they won’t be here till tomorrow so I didn’t know if I should wait on top them off till tomorrow or if they will be fine to do tonight. They look so yummy! I can’t wait to make them!!

  3. […] and makes some of  Like this Reese’s Pieces Chocolate Banana Bread, and Upside Down Pineapple Cupcakes and Pasta Primavera Casserole.  Oh, and these ham and pineapple kabobs she brought for you […]

  4. I’ve featured this recipe on my blog, hoping that you don’t mind, but if you do, please contact me and I’ll remove it. All the best.

  5. Love these cupcakes, totally gorgeous! Thanks for linking up with What’s Cookin’ Wednesday!

  6. My mom used to make pineapple upside down cake all the time! It was so fun to watch as she first put the fruit int he pan and then the cake batter. As a kid I was amazed by this cake, so silly. I bet these cupcakes are just as good, they look fabulous!
    Rachel @ I Love My Disorganized Life recently posted…A Few of My Favorite Things {Birthday} GiveawayMy Profile

  7. Oh wow…. these cupcakes look incredible! :) Thank you for sharing at Marvelous Mondays this week!
    Carrie @ Frugal Foodie Mama recently posted…Cookies & Cream Pie {A Guest Recipe from Mom’s Busy Helper}My Profile

  8. […]  Upside Down Pineapple Cupcakes Share this:FacebookEmailStumbleUponPrint (function(d, s, id) { var js, fjs = d.getElementsByTagName(s)[0]; if (d.getElementById(id)) return; js = d.createElement(s); = id; js.src = "//"; fjs.parentNode.insertBefore(js, fjs); }(document, "script", "facebook-jssdk")); This entry was posted in Entertaining, Ethinc, holidays, Plaid and Paisley Original Recipes, Side Dishes, Vegetarian and tagged 4th of july, blueberries, blueberrysalsa, salsa by Chandra@The Plaid and Paisley Kitchen. Bookmark the permalink. […]

  9. Thanks for sharing this at Wonderful Food Wednesdays – these look so yummy! I’m pinning them to my cupcake board now and following you there, too. :)
    – Ang

  10. These cupcakes look and sound amazing! Seriously dying to try them out! I bet my boys would love them!

    ~Jen @
    Jen Nikolaus recently posted…Best Ever Pasta Salad Recipe (with homemade dressing)My Profile

  11. You have such a beautiful site! I love the design. I found you through Tursday’s Treasures!

    Your cupcakes not only sound delicious, but they LOOK GORGEOUS! I will definitely have to pin this. I love pineapple…great summer flavor to infuse. Yum!

    Tammy (& Catherine) of Living the Gourmet
    Tammy recently posted…“BBQ” Style Chicken ThighsMy Profile

  12. This might just be the best cupcakes ever!
    Chung-Ah | Damn Delicious recently posted…Fried Avocado with Chipotle Cream SauceMy Profile

  13. These are BEYOND gorgeous Chandra! LOVE them. Pinned!
    Dorothy @ Crazy for Crust recently posted…Blueberry Crumb PieMy Profile

  14. Stephanie S. says:

    These look and sound so amazing! I can’t wait to make them :)

  15. Love these, Chandra! A perfect summer treat!
    Ashley @ Kitchen Meets Girl recently posted…What’s In Your Kitchen WednesdayMy Profile

  16. These are so cute Chandra! And I’m sure DELICIOUS! Pinned and shared on Facebook!
    Trish – Mom On Timeout recently posted…Peanut Butter and Jelly Sugar Cookie PizzaMy Profile

  17. These cupcakes look delicious! Love any kind of pineapple cake!
    Nancy P.@thebittersideofsweet recently posted…Soft Serve Raspberry Frozen YogurtMy Profile

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