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Preheat the oven to 350 degrees.
Line a cupcake pan with 24 cupcake liners.
In a large bowl or bowl of a stand mixer, add the cake mix, eggs, oil, water, cream of coconut, 1 teaspoon of the coconut rum, and crushed pineapple. Beat on high for 3 minutes.
Fill each of the cupcake liners ⅔ full with batter, transfer the pan to the oven, and bake for 12-15 minutes, or until a toothpick inserted into the center of a cupcake comes out clean.
Cool cupcakes for 1-2 hours.
To prepare the frosting, add the frosting and remaining 1 teaspoon of coconut rum to a bowl and beat for 2 minutes.
Add frosting to a piping bag equipped with the 1A tip, and squeeze frosting into the center of each of the cupcakes.
Top with a maraschino cherry and sprinkle of coconut.