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Sep 6, 2016 4:16 PM in response to Thomas Whaleyby BenB,Depends on the i/o device you're using, or the USB mic. Go to the System Preferences and set up inputs and outputs there. Then you should be able to do headphone monitoring. NEVER plug headphones into an i/o device or USB mic interface directly. Always go through the Mac's output, to head what is being recorded, not what the mic is picking up raw.