Single Pineapple Upside Down Cupcake

Easy Pineapple Upside Down Cupcakes with Rum: my take on a pina colada!

Yum
Pineapple Upside Down Cupcakes with Rum - no frosting
Before the buttercream…look away, it’s naked!

This weekend I went home to good old Michigan to visit my parents, and while I was there we created these Pineapple Upside Down Cupcakes with Rum, which is Volume 4 of my Boozy Bakes series! I had to do a little experimenting to get these little guys just right, but I really loved the way they turned out. Sweet, sticky, fluffy, and with that zing that comes from coconut rum? Yes please. But more on that in a minute.

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I love visiting my parents, and while I am there I always have two realizations:

  1. The second I enter their house, I am instantly, involuntarily, irrevocably twelve years old again.

2. Unfortunately, they were probably RIGHT about SO MANY THINGS throughout my life, and honestly that’s really annoying.

Baking and Photography in Michigan…

My dad did me a huge favor and gave me an emergency crash course in food photography this weekend. He is a man of many talents, and one of them is definitely photography. I am constantly amazed by his nature photos (check out his work here) as well as the depth of his knowledge about art in general. He did his best to impart years of photoshop knowledge in ten minutes, casually throwing out terms like “composition” and “clone brush” while explaining the difference between the lighting adjustments while I frantically scribbled notes and surreptitiously googled unfamiliar terms. I sure wish I would’ve paid attention to…. well, everything he ever said about photography, because now I really need to know it all. If only I had been listening instead of watching Gilmore Girls and reading fantasy novels my entire childhood. Oh well, you live, you learn.

Has my photography improved, though? I think yes. Thanks Dad!

Single Pineapple Upside Down Cupcake

My mom is also frustratingly wise, which makes my inner teenager roll her eyes. All those times she told me I should wear a slip with my skirt. Yeah, she was right. Wash my stage make up off before going to bed? Right again. Do my laundry every week instead of letting it pile up into an enormous closet-eating monster until I am finally forced into doing fourteen loads when I at last run out of socks six weeks later?

Nope. I’m still in denial about that one. I hate laundry and I can always just buy more socks.

BUT when she told me I should do some tests of this recipe before baking all of the batter at once, she was definitely right.

Pineapple Upside Down Cupcakes with Rum: the elements.

I knew I needed to do a pina colada cupcake to continue with my boozy bakes, but it didn’t seem right to do just a basic cupcake with filling and frosting for such an exotic cocktail. So I decided to lose the cupcake liners, grabbed my coconut rum and cake flour, did some research on a American classic bake, and came up with these Pineapple Upside Down Cupcakes with Rum.

I started with a can of pineapple rings. I drained them, dumping that sweet juice into a saucepan with brown sugar and a bunch of butter. Butter is my second favorite food (after mayonnaise) and this stuff smelled AMAZING as it melted down and turned into a pineapple sugar sauce. Honestly I would have been perfectly happy standing in the kitchen and eating this syrup all day. However, my mom kept stopping me and reminding me I needed them for the cupcakes. I also caught my dad sampling it a few times, so it wasn’t just me, I swear.

I drizzled this syrup in the bottom of a silicon cupcake tin, added some pineapple and maraschino cherries, and topped everything with a nice coconut cupcake batter.

Coconut Buttercream

These little guys are topped with a coconut buttercream liberally spiked with coconut rum, but honestly they could be served several ways. You could heat them up and serve them with ice cream, you could top them with whipped cream, or you could just eat them plain. I added this buttercream, though, because I was looking for a creamy element, I wanted to reinforce the coconut flavor, and as I mentioned before, I love butter. I mean. Come on. Who doesn’t? Coconut extract can be hard to find, but you can always get it on amazon.

Want to check out more Boozy Bakes? Find the easy recipes and my questionably funny anecdotes here:

Baileys Mudslide Cupcakes

Caramel Appletini Cupcakes

Tequila Sunrise Cupcakes

Want to order these cupcakes or any other recipe or custom cake from Kelly Likes to Bake? Email me at kellylikestobake@gmail.com

Enjoy this recipe, let me know in the comments how it goes!

Easy Pineapple Upside Down Cupcakes with Rum!

Recipe by Kelly Likes to BakeCourse: DessertCuisine: American BakingDifficulty: Medium
Servings

12

Cupcakes
Prep time

30

minutes
Cooking time

40

minutes
Calories

300

kcal

Ingredients

  • For the cupcakes:
  • 1 20 oz can of pineapple rings (juice reserved)

  • 12 tablespoons unsalted butter (cubed), in two portions

  • 200 g light brown sugar

  • 12 maraschino cherries (well drained)

  • 2 room temperature large eggs

  • 150 g sugar

  • ½ cup canola oil

  • 1/2 cup sour cream, room temperature

  • ½ cup milk, room temperature

  • 1 teaspoon vanilla extract

  • 1 teaspoon coconut extract

  • 3/4 cup coconut rum

  • 250 g all-purpose flour

  • 1 teaspoon baking powder

  • 1 teaspoon baking soda

  • 1 teaspoon salt

  • For the coconut buttercream:
  • 2 sticks unsalted butter, room temperature

  • 3.5 cups powdered sugar

  • pinch of salt

  • 1 teaspoon coconut extract

  • 1/3 cup coconut rum

Directions

  • In a small saucepan, combine the brown sugar, the pineapple juice, and 4 tablespoons of the butter. Cook it over medium heat until the sugar is dissolved and it is a little bubbly. Set it aside while you make the sponge batter.
  • Preheat your oven to 350 degrees F
  • Cream the remaining butter and sugar together with the paddle attachment of your stand mixer or with your hand mixer. When it is light and fluffy, add the eggs, one at a time, mixing well after each addition. Add the oil, sour cream, milk, coconut extract, and vanilla. Mix until just combined. Add the baking powder, baking soda, and half the flour. Mix until just combined. Add the rest of the flour, mix until just combined.
  • Pour a few tablespoons of your pineapple syrup in the base of each cup of your cupcake tin. Don’t be shy with it, the cake will soak it up. Add a few pieces of the pineapple rings and some maraschino cherries. Keep in mind that the pineapple will eventually be the top of your cupcake, so arrange it artfully if possible. Top with spoonfuls of the cupcake batter.
  • Bake in your preheated oven for 16-18 minutes or until an inserted toothpick comes out clean.
  • Cool COMPLETELY before attempting to flip out of the tin. I actually stuck mine in the freezer for a few minutes, and that was a good decision.
  • Make your buttercream frosting. Whisk the butter until light at fluffy. Add half the powdered sugar and the salt, coconut extract, and half the rum. Mix. Add the rest of the ingredients, whisk well. Adjust the consistency by adding more sugar or rum as necessary.
  • Frost your cooled cupcakes with an piping bag if desired, or just plop it on with a knife! Enjoy!
Cupcakes with all ingredients

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