Pineapple Inside-Out Cupcakes

It’s that time of year again.


I don’t know about you, but for the last however many years, once mid-February rolls around, I am so, so ready for a vacation. I used to think it was the snowy, endless New England winters that would have me feeling that way, but here I am now in California with my windows wide to a gorgeous 70 degree day.

And yet at least once a day I start daydreaming about hopping on a plane.

Anyone ever taken the Myer-Briggs personality test? I am an INFJ, which evidently means I’m “an idealist and a dreamer” yet “endeavor to take practical steps towards making ideals a reality.”

I don’t know if that’s a good or a bad thing, but I do know it’s made my wallet a lot lighter more than once. You see, every year I get my wanderlusty “dreams” going, and then I start taking those “practical steps” towards making them happen. Next thing you know I’m printing out a plane ticket and notifying my boss I’ll be gone for two weeks over the summer.

In recent years…

  • 2015: Hawaii and the UK
  • 2014: Cross-country USA road trip
  • 2013: Italy
  • 2012: Retreat in the Berkshires
  • 2011: Austria and Hungary

And plenty of little getaways in between. You see, I always have a legitimate reason to go, other than just taking a vacation. A conference to speak at, a performance to sing… I find some excuse.

All I know is I am itching to plan a trip. I’m tossing some ideas around in my head, but that “reason” has not appeared yet. Any suggestions?


While I wait to figure out where my next summer adventure will be, there’s cupcakes. Pineapple Inside-Out Cupcakes! Coconut, pineapple, rum, and a cherry on top. It’s like a little vacation baked into a paper wrapper.

Well hardly, but we can pretend. These cupcakes are actually the last installment of the “marathon” of dessert recipes I shared from the recital I catered last week. I would have posted them along with the others, but I was interrupted by  National Margarita Day which took priority. After a week long break from all the sugar, err not quite, what better than a sweet treat for your weekend?

I baked my first upside down cake this past fall and fell in love. It was an apple-cranberry cake and so yummy. I’ve yet to make an actual pineapple upside down cake, but it is on my list! I couldn’t resist turning it “inside out” and baking it in miniature cupcake form for the reception. If you love pineapple upside down cake, and rum, or just cupcakes in general, I’m fairly certain you’ll love these.

Yes, they are a little time consuming, but they are worth the effort!

First you’ll make the filling so it has time to cool before assembling the cupcakes. Finely minced pineapple, brown sugar, some juice, and rum, warmed with a hint of spice and thickened by a little cornstarch. Make sure you hide your spoons so you don’t eat this all before it gets to the cupcakes.

The cupcakes are the buttery yellow cake that everyone loves about upside down cake, but I’ve used coconut milk and pineapple juice to make them extra tender. The coconut flavor comes through subtly and is such a complement to the filling and frosting.

Oh. The frosting. Put this on my list of better ideas I’ve had. It took me a while to decide how to top these cupcakes. I knew I wanted brown sugar flavor as that’s what distinguishes upside down cake. First I tried a cream cheese based frosting because that is my go-to. Um, a failure for sure. Then I tried a stabilized whipped cream deal that was maybe even more disappointing than my first attempt. Discouraged, I waited a few weeks before trying these cupcakes again. After opening a bottle of Sailor at the beginning of the month for these killer “snacks,” I started to wonder if it was possible to make simple syrup out of alcohol and sugar instead of water and sugar. I mean obviously the alcohol would cook out but would the flavor still come through?

It most certainly does. Brown sugar and rum, caramelized and reduced, then added to fluffy buttercream frosting once cooled. Holy moly. I’ve talked before about how I’m really particular about frosting and don’t really know anyone who likes super sweet buttercream. Considering this Caramelized Rum Buttercream is buttercream with sugary caramel added to it, don’t ask me how it’s not cloyingly sweet. Maybe it’s the same scientific phenomenon that happens with Starbucks drinks. 1/3 cup of sugar in a single cup yet still “just right”!

This frosting is totally different from any other you’ve probably eaten, and tops these Pineapple Inside-Out Cupcakes perfectly. Pineapple upside-down cake is good, but soft cake with thick pineapple jam centers and fluffy, rummy, buttery frosting? These Pineapple Inside-Out Cupcakes might just be even better. With a cherry on top, they’ll help make the days until your next vacation seem not so far away.


Pineapple Inside-Out Cupcakes

Yields 12 cupcakes

Buttery yellow cupcakes made with coconut milk and pineapple juice, thick spiced pineapple filling, and a swirl of fluffy caramelized rum buttercream. The flavors of pineapple upside-down cake turned inside out!


Pineapple Filling:
  • 2 cups pineapple, finely minced*
  • 3 Tbs. (37g)  brown sugar
  • ¼ cup pineapple juice
  • 1 ½ Tbs. lemon juice
  • 1 Tbs. rum
  • 1 Tbs. (8g) corn starch
  • 1/8 tsp. cinnamon
  • Dash of nutmeg
  • Dash of salt
  • 1 2/3 cup (210g) all-purpose flour
  • ½ tsp. baking powder
  • ¼ tsp. baking soda
  • ½ tsp. salt
  • ½ cup (57g) unsalted butter, softened
  • ½ cup (100g) granulated sugar
  • ½ cup (100g) brown sugar
  • 1 large egg, room temperature
  • 1 ½ tsp. vanilla extract
  • ½ cup light coconut milk
  • 1/3 cup pineapple juice
Caramelized Rum Buttercream:
  • ¼ cup (50g) brown sugar
  • ¼ cup rum
  • 1 cup (230g) unsalted butter
  • 3 cups (360g) powdered sugar
  • 1 tsp. vanilla extract
  • 2-3 tsp. heavy cream
  • Dash of salt
  • Dash of cinnamon


For the filling:

Combine the pineapple, sugar, and juices in a saucepan over medium heat and bring to a boil. Once boiling, turn the heat to medium low and simmer to reduce slightly. About 3-4 minutes.

In a small cup, stir the rum and cornstarch into a slurry. Pour it into the saucepan and whisk to combine. Add the spices and salt.

Cook the filling, stirring frequently, until it begins to thicken. This should take 1-2 minutes only. Remove from the heat and allow to cool slightly before transferring to a bowl. Chill in the refrigerator before assembling the cupcakes.

For the cupcakes:

Preheat the oven to 350º F. Prepare 18 cupcake liners.

In a medium bowl, sift together the flour, baking powder, baking soda, and salt, and set aside.

Cream the butter in a large bowl using either a stand mixer or a hand mixer. Add the sugars and continue to beat until fluffy. Add the egg and vanilla and beat until mixed in.

Whisk together the coconut and pineapple juice in a measuring cup or small bowl.

With the mixer on low, begin adding the flour in three batches, alternating each with the milk/juice mixture until everything is incorporated. Do not over beat!

Divide the batter evenly between the cupcake liners. Bake for 20-22 minutes, or until a toothpick inserted in the center comes out clean.

Allow the cupcakes to cool for 5 minutes in the pan before transferring to a cooling rack. Cool thoroughly before filling and frosting.

 For the frosting:

In a small saucepan set over medium heat, whisk together the brown sugar and rum. Bring to a simmer, then reduce the heat to low. Cook the mixture at a bare simmer, stirring frequently, until it has thickened into a thin syrup and reduced down to 2 Tablespoons. Remove from the heat and cool to room temperature before using.

In a large bowl, cream the butter using an electric stand or hand mixer until smooth and fluffy. Slowly add the powdered sugar a half cup at a time.

Once all the sugar is in the bowl, add the rum syrup, vanilla, and a dash of salt. Continue to beat the frosting at medium-high speed for 1-2 minutes. Stream the heavy cream into the bowl and beat until very light and fluffy, about 2-3 minutes longer.

To Assemble:

Using a paring knife, cut and remove a small cone from the top of each cupcake. To do this, angle the knife towards the center and insert it about a half inch from the cupcake’s edge, stopping a little below the center. Continue to hold the knife at an angle as you rotate the cupcake, making a circle about one inch in diameter. Lift the knife, and a small cone of cake will come out. Set aside.

Fill the cavity in each cupcake generously with the pineapple filling.

Pipe frosting over the top of the cupcakes, or simply spread it on with a knife. Decorate with maraschino cherries and little pineapple wedges, if desired. Uneaten cupcakes may be stored in an air-tight container in the refrigerator for up to four days. Bring to room temperature before eating.

*You may use either free pineapple, or pineapple chunks from a can that have been drained. Make sure to mince the pineapple very finely.



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