Preheat the oven to 350°F. Grease a bundt pan and lightly dust it with cocoa powder. Alternatively, prepare two 9-inch round pans or 24 cupcake liners.
In a large mixing bowl, combine sugar, flour, cocoa powder, baking powder, baking soda, and salt. Use a whisk to mix them well.
Add the eggs, milk, olive oil, and vanilla to the dry ingredients. Beat with a mixer on medium speed for about 2 minutes.
Gradually pour in the boiling water while stirring until everything is well blended. The batter will be quite thin—this is just right!
Pour the batter into your chosen pan(s) and bake: for bundt cake, 35-40 minutes; for 9-inch rounds, 30-35 minutes; or 22-24 minutes for cupcakes. Check for doneness with a toothpick.
Allow the cake to cool completely in the pan(s) before you frost it.
For the frosting, gently heat the cream in a saucepan until it is steaming, or use the microwave.
Remove from heat and add the chocolate chips to the hot cream. Allow it to sit for a few minutes, then stir until smooth and glossy.
Mix in the powdered sugar and cocoa powder to the chocolate, whisking until perfect.
Pour the luscious frosting over the cooled cake. You can enjoy it right away or chill in the refrigerator until the frosting has set.