Preheat your oven to 350°F (175°C). Line a muffin tin with cupcake liners.

In a large mixing bowl, combine the flour, sugar, cocoa powder, baking soda, baking powder, and salt. Whisk until well blended.

Add the egg, buttermilk, vegetable oil, and vanilla extract to the dry ingredients. Mix until just combined.

Gradually stir in the boiling water until the batter is smooth and well combined. The batter will be thin.

Pour the batter into the prepared cupcake liners, filling each about 2/3 full.

Bake for 18-20 minutes or until a toothpick inserted in the center comes out clean. Allow the cupcakes to cool completely in the pan before transferring them to a wire rack.

For the frosting, beat the powdered sugar, cocoa powder, softened butter, and vanilla extract in a mixing bowl until combined.

Gradually add milk, one tablespoon at a time, until the frosting reaches a spreadable consistency.

Once the cupcakes are cool, frost each cupcake generously with the chocolate frosting.

Place the frosted cupcakes in the refrigerator for about 30 minutes to set the frosting.

While the cupcakes chill, melt the chocolate chips and vegetable oil in a microwave-safe bowl in 30-second intervals, stirring in between until smooth.

Remove the cupcakes from the refrigerator and dip each one into the melted chocolate, allowing any excess to drip off.

Place the coated cupcakes on a wire rack to set.