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, 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.
Mix 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 fully combined.
Add a spoonful of graham cracker crunch to the bottom of the cupcake liner.
Fill cupcake liners with the chocolate cupcake batter to ¾ full. Use a large cookie scoop for even cupcakes.
Sprinkle the remaining graham cracker crumbs evenly over the batter.
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.