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, cocoa powder, instant espresso powder, and boiling water until the cocoa powder is dissolved. Set aside to cool slightly.
In a mixing bowl, combine all-purpose flour, granulated sugar, baking soda, and salt. Whisk to combine.
Pour the chocolate mixture into the dry ingredients and whisk until combined.
Add vegetable oil, eggs, and vanilla extract. Whisk until combined and smooth.
Portion the cupcake batter into the cupcake liners, approximately 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. Transfer the cupcakes to a wire cooling rack to cool completely.