Preheat the oven to 350°F, and line 21 muffin cups with parchment cupcake liners.
In a large bowl with a hand mixer or a stand mixer, beat the cake mix, eggnog, oil, eggs, rum extract, vanilla extract, nutmeg, and cinnamon on low speed for 30 seconds. Then, increase the speed to high and mix for 2 minutes, scraping down the sides of the bowl a few times during the process.
Pour the batter into the muffin cups using about 3 tbsp each (I use a 3 tbsp cookie scoop for this), then bake until the cupcakes are set and pass the toothpick test (13-18 minutes-mine were perfect at 15 minutes). Let the cupcakes stand in the muffin pan for 5 minutes before removing and placing them on a wire rack to finish cooling.
Pour the gelatin into a pyrex measuring cup or small bowl. Add the cold water and stir until all of the gelatin has been absorbed. Let it sit for 5 minutes. Add cold heavy whipping cream, powdered sugar, and both rum and vanilla extract to a chilled bowl (I place it in the fridge while the cupcakes are baking) and beat until thickened but not quite reaching soft peaks. If the gelatin has solidified, pop it into the microwave for 5-10 seconds until it has reliquified (you want it to be liquid but not hot). Stir until smooth. Turn the mixer back on low speed and slowly drizzle in the gelatin. Slowly increase the speed to medium-high and beat until soft peaks form (do not overmix- it should have the consistency of thick shaving cream so you can easily pipe it onto the cupcakes).
Once the cupcakes are cooled completely, use a piping bag fitted with a large star tip to swirl each cupcake with rum whipped cream frosting. No piping bag? Cut off the end from one corner of a zip-top bag to use as a piping bag.
Top each frosted cupcake with freshly grated nutmeg for the perfect finishing touch. Cheers!