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'Pineapple Upside-Down Cake' Inspired Mini Cupcakes with Coconut Milk Reduction Vanilla Frosting

I've been to dreamy mini-cupcake heaven and back today making these. Ever since I was little, my all-time favorite cake has been Pineapple Upside Down Cake. I think I can pinpoint this love of mine to pure nostalgia.

When my family was still pretty young, we'd hook up our boat (which seemed completely humongous to us 3-12 year olds at the time) and make the long trip to beautiful Lake Powell. My Mom fed us almost every night from the dutch oven - including dessert. It was then was when I was introduced to Pineapple Upside Cake for the first time. The fluffy and moist yellow cake smothered with brown sugar-soaked warm pineapple and maraschino cherries melted in my mouth. Since then, no other cake can come in at a close second in my eyes.

Tonight the ladies are having a little get-together, and have been asked to bring cupcakes! I, of course, went straight to the store to buy the never-failing Pineapple Supreme Pillsbury cake mix. I was surprised to not see it anywhere on the shelves. I was so confused. How could they have box after box of carrot cake mix, and NO pineapple? Cue the panic session.

If you're still not convinced of my diehard love of this cake, let me tell you how the rest of the morning went down: I drove to 3 other local grocery stores to find this cake mix (only to be stabbed by the shelves loaded neatly with ANY other cake mix imaginable... but no trace of Pineapple Supreme). At the last store, I called it quits, and left with yellow cake mix. Apparently my fetish wasn't worth mass production of Pineapple Supreme cake mix, or perhaps everyone knows how awesome it is, and bought out all the 4 stores I visited. Not likely, but I'm praying that's the reason.

I know pineapple upside-down cake isn't typically served right side up (hence the name), or put frosting on it (hence the name, again) but I wanted to do something different. So I broke both the aforementioned rules. And I think it was a tasty success. I can't wait to take them to the girls tonight!


'Pineapple Upside-Down Cake' Inspired Mini Cupcakes
with Reduced Coconut Milk Vanilla Frosting

1 box yellow cake mix (I prefer Pillsbury Super Moist - the pudding in the mix is to die for)
3 eggs (according to whatever box mix you buy)
1/3 cup oil ''
1 jar maraschino cherries, sliced in half
1 can crushed pineapple
about a half cup of brown sugar
about a half cup of butter

1 cup (2 sticks) unsalted butter, room temperature
2 1/2 cups powdered sugar
1/3 cup reduced coconut milk (I found it in the Latino section), room temperature
Seeds scraped from 1 split vanilla bean or 1 1/2 teaspoons vanilla extract
1/8 teaspoon salt

1 1/2 cups sweetened flaked coconut, lightly toasted (for garnish)

For reduced coconut milk:
Bring coconut milk to boil in large deep saucepan over medium-high heat (coconut milk will boil up high in pan). Reduce heat to medium-low; boil until reduced to 1 1/2 cups, stirring occasionally, 25 to 30 minutes. Remove from heat; cool completely. Transfer to small bowl. Cover; chill (coconut milk will settle slightly as it cools). DO AHEAD: Can be made 2 days ahead. Keep chilled. 

For cake:
Preheat oven to 350 (I did 325 because I was using a non-stick dark sheet). In a mixing bowl, add cake mix, eggs, oil, and pineapple juice (from your crushed pineapple - I had almost a cup) and mix until there aren't any little pockets of powdery mix. Add your mini cupcake liners to your mini cupcake pan. In the bottom of each little cup, add a teeny bit of butter, and brown sugar. Add one cherry to each cup, then add a little pineapple. Coat the pineapple and cherry with enough cake mix to barely cover*. I have 12 cupcakes to a pan, so I only put them in the oven for 10 minutes. Let them cool, and frost!

For frosting:
(adapted from
Using electric mixer, beat butter in large bowl until smooth. Add sugar, 1/3 cup reduced coconut milk, seeds from vanilla bean, and salt. Beat on medium-low speed until blended, scraping down sides of bowl. Increase to medium-high and beat until light and fluffy. Using pastry bag fitted with large star tip, pipe frosting onto cooled cupcakes. (Alternatively, top each cupcake with 2 tablespoons frosting. Using small offset spatula, swirl frosting over top of cupcakes, leaving 1/2-inch plain border.) Sprinkle with coconut. DO AHEAD: Can be made 1 day ahead. Store in airtight containers; chill. Bring to room temperature before serving. 

*Alright - it's very very very important to not overfill these things. With everything in the cup, you should be about 1/2 at least, or 3/4 at most full.

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  1. oh wow! Can i have one!?

    Found you on TT & J and would love for you to come by join us on our linky party and link this up! :)


    Angie from ALI

    1. I'd love to! Thanks for the invite, I linked it right up. Your blog looks fantastic, btw.

  2. Replies
    1. They really were - we gobbled them up so fast! With them being such little cupcakes, it was hard not to just pop the while thing in our mouths.

  3. YUM! Can't wait to try these. Thanks for linking up to our "Strut Your Stuff Saturday." We love having you and hope you'll be back next week! -The Sisters

    1. Thanks so much for hosting such a popular party! You guys are the best.

  4. I love pineapple upside down cake! I'll have to try these.

    1. Isn't it just the best? I've always had it at the top of my list. Thanks for stopping by! You'll absolutely love these.

  5. Were the bottom of the liners soggy?

    1. Yep - anytime you line the bottom of a cupcake liner with a little butter (in our case here, the butter/brown sugar/cherry/pineapple) it will be moist.

    2. Did they leak everywhere? Sorry, I ask these questions because I want to make these for a big birthday bash but would need to keep them in the cupcake liners for the display. Would these work or will they leak and be too messy? I'm looking for a good cupcake recipe that mimmicks the original pineapple upside down cake recipe without having to actually flip it upside down.

    3. Your questions are perfectly fine! Way to plan ahead, girl! I don't think they'd be messy at all. My liners were a little wet, but I bet if you doubled the liner, or even just added another liner after you baked them, you should be alright. Definitely not enough to be a mess by any means. When I held them in my hands, it didn't leave any marks or wetness, if that helps. Good luck with everything! I promise they'll be a hit!

  6. It looks irresistible! Cant wait to try it out sometime soon!


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