Abstract: A chatbot system and method with contextual input/output messages. A chatbot includes a processor, an interactive dialog interface and a knowledge database. The system uses a script file to display input and output messages in a tree format. An initial input or output message is stored. An identifier is assigned to the initial input or output message that is then used as context for the subsequent input/output messages by associating and storing the identifier with the subsequent input/output messages. The relationship between the first input or output message and subsequent input/output messages define a parent-child relationship that is displayable via the script file.