Preheat the oven to 350 degrees.
Line a muffin tin with 12 cupcake liners and set aside.
In a large bowl cream together the butter and sugar. Add in the eggs and beat until combined. Stir in the vanilla.
In a medium bowl combine the flour, cocoa powder, baking powder, and salt. Mix well.
Add half the flour mixture to the butter mixture and mix well.
Heat the milk for 30 seconds in the microwave so it is just warm. This will help the cocoa powder mix into the batter. Pour into the bowl with the butter and mix until well combined.
Add the remaining flour and mix until just combined.
Fold in the chocolate chips.
Divide the mixture between the muffin cups and bake for 22-24 minutes.
Remove from oven and cool completely on a wire rack.
To make the frosting beat the butter in a large bowl on medium speed until smooth.
Add in the powdered sugar a half cup at a time, mixing after each addition, until well combined.
Add the cocoa powder, milk, and vanilla and beat on high speed until desired consistency is reached.
Pipe the frosting onto the cupcakes and top with a chocolate caramel truffle and chocolate jimmies.