Preheat oven to 350° F. Line a cupcake pan with 12 cupcake liners.
In a small bowl or a glass liquid measuring cup, stir together semi-sweet chocolate chips, dark cocoa powder, and boiling water until the chocolate chips are melted. Set aside.
In a large mixing bowl, whisk together all-purpose flour, granulated sugar, baking soda, and salt.
Stir the chocolate mixture again to ensure that the chocolate chips are melted. Pour the chocolate mixture into the dry ingredients and whisk gently until just combined.
Add vegetable oil, eggs, and vanilla extract. Whisk until the batter is well combined and smooth.
Portion the cupcake batter into the 12 cupcake liners. Use a large cookie scoop or pour into the cupcake liners with a large liquid measuring cup.
Bake for 20 minutes or until the tops of the cupcakes bounce back slightly when gently touched or a toothpick comes out clean.
Remove the cupcakes from the oven and cool in the pan for a few minutes before transferring the cupcakes to a wire rack to cool completely.