Begin by preheating your oven to 350°F (175°C). Line your cupcake tin with paper liners and set them aside.
In a medium-sized mixing bowl, combine the sifted cocoa powder, flour, baking soda, baking powder, and salt. Whisk the dry ingredients together until well mixed and set this bowl aside.
In the bowl of your stand mixer, beat the softened butter on medium speed until it's smooth and creamy. Slowly add the vegetable oil and vanilla extract, mixing until everything is fully incorporated. Gradually add in the sugar, beating on medium-high speed for 4 to 5 minutes, or until the mixture becomes fluffy and light.
One by one, add the eggs into the butter mixture, ensuring each is well combined before adding the next. Scrape down the sides of the bowl as needed to ensure everything blends evenly.
Reduce the mixer speed to low, and alternately add the dry ingredient mixture and the milk to the wet mixture, starting and ending with the dry ingredients. Do this in 3 parts for the dry ingredients and 2 parts for the milk. Mix until just combined—be careful not to overmix.
Slowly add the hot coffee into the batter while the mixer runs on low speed. The batter will be thin, but this is exactly what you want.
Scoop about ¼ cup of batter into each cupcake liner, filling them approximately two-thirds full. Bake for 16-18 minutes, or until the tops spring back when lightly pressed or a toothpick inserted comes out clean with just a few moist crumbs. Baking times may vary, so start checking a couple of minutes before the recommended time.