Preheat oven to 350° F. Line a cupcake tray with 12 cupcake liners.
In a small bowl or a glass liquid measuring cup, stir together chocolate chips, cocoa powder, and boiling water until the cocoa powder is dissolved and the chocolate chips are melted.
In a mixing bowl, combine all-purpose flour, sugar, baking soda, and salt. Whisk to combine.
Pour the 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.
Fill cupcake liners ¾ full.
Bake 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 cool completely.