The performance of the Graphene/Si (Gr/Si) Schottky interface and its potential in future electronics strongly relies on the quality of interconnecting contacts with external circuitry. In this work, we investigate the dominating and limiting factors of Gr/Si interfaces designed for high light absorption, paying particular attention to the nature of the contact failure under high electrostatic discharge (ESD) conditions. Our findings indicate that severe current crowding (CC) at contact edges of the graphene is the dominating factor for the device breakdown. Material degradation and electrical breakdown are systematically analyzed by atomic force, Raman, scanning electron, and energy-dispersive X-ray spectroscopies. This work enlists the robustness and limitations of Gr/Si junction in photodiode architecture under high ESD conditions that can be used as general guidelines for 2D-3D electronic and optoelectronic devices.