Pineapple-Rum Upside Down Cupcakes

Sweet, juicy pineapple-infused cupcakes are crowned with a brown-sugar rum caramel and a circle of crushed pineapple. A maraschino cherry adds the finishing touch of sweetness and a pop of color. This recipe also translates well to cake form!


Hey friends! I'm back from (presumably) the dead!

...ok, maybe not quite. But, I do apologize for being off the grid! I've spent the past week working, eating, drinking, eating, karaoke-ing, and drinking my way through the lovely city of Detroit, Michigan. My whole body hurts. But, I'm back in DC (my happy place) and that's all that that matters!


Before I embarked on Operation #DetroitNeverSleeps, my roommates and I celebrated the onset of summer by hosting a luau-themed party. By this, I mean that the Facebook event name was "Get 'Lei-d' in Clarendon!" and the event photo was the following:


On Saturday morning, Lexi and I headed to Giant to stock up on the essentials - aka chasers, pina colada mix, and the ingredients for these cupcakes! (I already had tequila, the #1 essential, otherwise that would have been HIGHEST priority). While we were out, I got what I can confidently say is the best. text. ever.

AmazonYour package containing '25 assorted Hawaiian leis and 144 mini cocktail umbrellas has been delivered.'


I almost had a stroke. Luckily, Lexi had the smelling salts at the ready and was able to revive me, just in time for me to dash downstairs and grab the magical package. We. Were. Ready.


We pumped up the jams in the kitchen, and I got to work on the...

Pineapple-Rum Upside Down Cupcakes


To make these cupcakes, you will need:
- 1 box yellow cake mix (if you're ratchet and lazy like me) + ingredients required by box (oil and eggs, most likely, but this may vary by brand)
- 1 can crushed pineapple, drained; juice reserved
- 1 stick unsalted butter
- 1/4 cup rum (I used Bacardi silver)
- 1 cup dark brown sugar
- 1 jar maraschino cherries

To begin, preheat your oven to 350F and spray two cupcake tins well.

Rum Caramel Sauce
In a saucepan over medium heat, melt your butter. Once the butter has melted, stir in the brown sugar and rum. Continue cooking, stirring frequently, until the sugar has dissolved completely. Remove from heat, and let cool completely while you prepare the...

Pineapple Cake
In a large bowl, combine the yellow cake mix with the ingredients called for on the box, but with one little change - you will replace the water in the recipe with the reserved pineapple juice. Stir this together until just combined, and then set aside.

Assembly: In the bottom of each cupcake tin, dollop about 2 tablespoons of the rum caramel. On top of this, place 1/2 a maraschino cherry and then a circle of crushed, drained pineapple (is it just me, or does it sound like this pineapple has had a very bad day?!). Finally, layer in the cake batter until each tin is about 3/4 full. If you have leftover batter, caramel, and fruit, break out a cake pan for the rest of it!*


*I admit, I only have ONE cupcake tin (1. Uno. Please send more my way, I'm impoverished) so I just made 12 cupcakes and a cake. No one complained about it...

Bake for 17-19 minutes, or until a toothpick inserted in the center of the cupcake comes out clean. Remove from the oven and let these cool for about 15 minutes.

Now, here's the tricky part - getting them out of the pan. I recommend running a butter knife around the outside of each cupcake to loosen them from the tin, and then just going for it and flipping the whole pan over. Take a leap of faith, guys. It WILL work out.


And, there you have it! Let me tell you, these were a HUGE HIT. So moist, and sweet, and perfect for our luau! Which, by the way, was awesome. Drunk jenga and dancing never fail to impress. Plus, we went out in our leis, which essentially guaranteed an unbeatable night.


I am honestly just thrilled that I live in a world where I can wear 3 leis to a party and put 2 umbrellas in my tequila. Peace 'n blessins, y'all.