Actually you sort of can. For example, if you have the output set to the analog out in the system settings and you go into VLC and set the output to digital, you can have two independent outputs at the same time (VLC will output digitally, and the rest of the system such as iTunes, etc. will go through the analog). I am assuming however you want to mirror the same audio content, which I am not sure you can do. But given what is possible with my example above it seems the hardware should be capable.