Embodiments provide systems, methods, and computer program products for network management application to automatically determine a session prompt for a network device and perform error handling. After logging in to a network device, the network management application records the first session prompt response. The network management application sends a series of empty carriage returns and random characters and records the session prompt responses. The network management application compares the responses and determines whether the prompt is a static or a dynamic prompt based on the results. The network management application elicits error responses from the network device by sending additional random characters and records the results in an error handling dictionary. The error handling dictionary is used later when running user-provided commands, enabling a determination of whether a command executed successfully.