A method and system for capturing and reporting debug information regarding data transport failures in a multi-level secure operating environment. A process available only to a trusted system administrator is activated causing probe activation. The data transport command is repeated. The process probes the locations where the data packets move across environment boundaries of the secure network. When the data stops being transported, the process captures the relevant information on the type of failure, its cause, the address where it occurred and the possible consequence. The captured information can then be displayed to an appropriately credentialed administrator through a password-protected command for debug. The probes are then deactivated.