Systems and methods for error detection within a multi-session collaborative environment. One method includes receiving, from a first client application session associated with a first user, a first diagnostic log, including an error message. The method includes determining a second client application session associated with a second user in a collaboration session with the first client session, and triggering, in the second client application session, an artificial error condition based on the error message. The method includes, receiving, from the second client application session, a second diagnostic log. The method includes tagging the first and second diagnostic logs with a session identifier indicative of the collaboration session, and transmitting the first and second diagnostic logs to a collaborative environment administrator. The method includes transmitting a notification based on the error to at least one of the first client application session and the second client application session.