Millsy

assuming you definitely chose the correct playback device (easy to choose the wrong one ), then I don't know sorry

Its possible to output to two sources, although i'm not sure it works as you'd want to it too (one might be slightly behind the other) but anyway's here is how I would do it (doesnt have to be "what u hear", stereo mix is the same thing) From here, select the desired device (what u hear/ stereo mix) and go to properties - listen Select listen to this device and obviously select your second output. I think this works with multiple outputs