Collecting debug information includes facilitating a communication session for an endpoint operated by a user. One or more user-driven conditions are monitored, where a user-driven condition results from an action by the user. Data is gathered during the monitoring. Whether the communication session is satisfactory or unsatisfactory is determined from the one or more user-driven conditions. Monitoring is discontinued if the communication session is satisfactory, and debug information is generated from the gathered data if the communication session is unsatisfactory.