I have had the exact same issue with the headphone out. I have an incredible sound coming through my monitors and when recorded, however, when I use the headphones its very brittle and digital sounding. It sounds like the cab sim is turned off, but obviously that is not the case. Too bad, it would be sweet to get that great tone through the headphones too. I understand that it may be off due to different types of headphones, but this is a HUGE difference. It sounds so digital and just terrible, nothing like how great the Axe II sounds through everything else.