A system and method is disclosed herein for providing a bidirectional outage bypass for a hosted voice-over Internet protocol (VoIP) private branch exchange (PBX) system. An outage monitoring system is in communication with both the bidirectional bypass system and one or more bypass enablers that act at the direction of the bidirectional bypass system. The outage monitoring system detects outages and overloads, as well as, network failures between the VoIP PBX and the public switched telephone network (PSTN). The bidirectional bypass system, in response to detection of an outage, determines error-handling procedures for the bidirectional bypass based on bypass configuration data. The bypass enablers forward outgoing communications between a client device and the PSTN, in accordance the error-handling procedures, by bypassing components that are currently experiencing failures or overloads. The bypass enablers forward incoming communications for the VoIP PBX to an alternative destination in accordance with the error-handling procedures.