A system and method for cognitive journey monitoring are presented. Embodiments comprise journey prediction, parsing of data sources, risk assessment and mitigation, and natural-language user interaction by a cognitive processor. Data is gathered from a plurality of data sources and analyzed in the context of one or more of the user's intention(s). A dialogue with the user, in natural language, aims to provide and select one or more suggestions relating to the one or more user intention(s) such that the risk(s) relating to the one or more user's intention(s) is reduced. During the dialogue, cognitive reasoning may be performed, wherein the cognitive reasoning includes the ability to justify each suggestion and the ability to infer information from the interaction such as, for example, data obtained in a dialogue may inform subsequent inferences. The embodiments may use speech synthesis and speech recognition in an interactive spoken dialogue.