- For the cupcakes: 
- Preheat oven to 350 degrees F. 
- Line 28-30 muffin tins with cupcake liners and set aside 
- Sift together the flour, cocoa powder, baking powder, baking soda, and salt in a medium size bowl. 
- Add sugar and stir to mix. 
- Pour flour mixture into a large mixing bowl and add eggs, oil, milk and vanilla. 
- Beat on medium speed for 2 minutes, then stir in boiling hot water (consistency will be thin). 
- Fill cupcake liners 2/3 full with batter. 
- Bake for 20-25 minutes (oven temps can vary), or until a toothpick inserted into the center comes out clean.  Cool completely while you make your frosting.  
- For the frosting: 
- Place butter into the bowl of a stand mixer and beat with whisk attachment until creamy. 
- Add one cup of powdered sugar and blend until smooth. 
- Add vanilla, milk and cream, then continue slowly adding sugar until all is incorporated and frosting is smooth and creamy. 
- Stir in chocolate chips and frost on cooled cupcakes. 
- *Store cupcake in a sealed container in the refrigerator until ready to serve