Systems and methods are provided for detecting a potential ambiguity in a sequence of clearance communications using conversational contextual information to identify potentially related communications. One exemplary method involves obtaining a first clearance communication associated with a first aircraft, obtaining a second clearance communication associated with a second aircraft, identifying a first conversational context associated with the first clearance communication, identifying a second conversational context associated with the second clearance communication, identifying a discrepancy between the first clearance communication and the second clearance communication based at least in part on the first conversational context and the second conversational context, and in response to identifying the discrepancy, generating a user notification at one of the first aircraft and the second aircraft.