Preheat your oven to 350°F (175°C). This ensures your cupcakes bake evenly.
Line your muffin tin with cupcake liners. This not only makes for easy cleanup but also adds a lovely touch to your presentation.
In a large mixing bowl, whisk together the granulated sugar, all-purpose flour, Dutch processed cocoa, baking powder, baking soda, and salt until well combined.
Add the eggs, whole milk, canola or vegetable oil, and vanilla extract to the dry ingredients. Mix until just combined. The batter will be thick and rich.
Carefully stir in the boiling water. This step is crucial as it helps to create a moist cupcake. The batter will now be thin, which is perfectly normal.
Gently fold in the semi-sweet chocolate chips, ensuring they are evenly distributed throughout the batter.
Pour the batter into the prepared muffin tin, filling each liner about two-thirds full. This allows room for the cupcakes to rise beautifully.
Bake in the preheated oven for 18-20 minutes or until a toothpick inserted into the center comes out clean. Be careful not to overbake!
Once baked, remove the cupcakes from the oven and allow them to cool in the tin for about 5 minutes. Then, transfer them to a cooling rack to cool completely.