Charge accumulation severely limits the reliability of photoemission measurements in diamond, particularly under high photon flux conditions where continuous electronic refilling is required. Here, we investigate the charging mechanisms in diamond structures embedding laser-written graphitic microchannels, combining spatially resolved synchrotron-based photoemission with controlled surface conditions. The presence of conductive graphitic channels does not ensure effective charge compensation, which instead critically depends on the formation of a conductive network involving surface adsorbates and/or electronically active overlayers. This result reveals that the interplay between buried conductive channels, nature of the adsorbates, and measurement geometry determines the stability of electron emission. These findings define design rules for diamond based systems with controlled charge transport, enabling reliable surface spectroscopy and microscopy while accelerating progress toward stable diamond electron emitters.