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 chocolate chips, dark cocoa powder, and boiling water until the chocolate chips are melted. Set aside to cool.
In a mixing bowl, whisk together all-purpose flour, granulated sugar, baking soda, and salt.
Pour the melted chocolate mixture into the dry ingredients and whisk gently until just combined.
Add vegetable oil, eggs, and vanilla extract. Whisk until fully combined and smooth.
Portion the cupcake batter into the cupcake liners to about ⅔ full. Use a large cookie scoop or pour the batter into the cupcake liners using a large liquid measuring cup.
Bake the cupcakes for 20 minutes or until the tops of the cupcakes bounce back slightly when touched.
Remove from the oven and cool in the pan for 5 minutes. Remove the cupcakes from the pan and transfer to a wire rack to cool completely.