Line a cupcake pan with cupcake liners (you might need a couple more, sometimes this recipe makes a dozen cupcakes, sometimes 14). Preheat the oven to 350 degrees F (177 C). Preheat more than enough water on the stove (or however you want), so that it will be boiling when it's time to mix into the batter.
In a medium-sized bowl, whisk the GF flour, cocoa powder, baking powder, baking soda, and salt together until there are no cocoa lumps. In a large bowl using an electric hand-mixer (you could also use a stand mixer), whip the sugar, oil, and eggs together until light and fluffy.
Add half of the dry mixture and mix until combined. Pour in the vanilla and milk of choice and mix until incorporated. Add the remaining dry mixture and mix until completely smooth. Scrape the sides and bottom of the bowl with a spatula to ensure nothing goes unmixed. While the mixer is running on low-speed, carefully pour in the boiling water. Once it is added, turn the mixer to high and mix very well.
Distribute the batter between the cupcake liners, filling each one ⅔ full. Bake for 15-20 minutes or until a toothpick comes out clean. Let the cupcakes cool completely at room temperature.