Systems are provided for providing contextualized user recapture solutions. A user interaction contextualization system may receive a notification of a user accessing one of the organization's services via a user device. Responsive to the notification, the user interaction contextualization system may collect and analyze contextual data from various data sources, and real-time and historical user engagement data associated with the user. The user interaction contextualization system may then use the collected data to determine the user's likelihood of abandonment of the organization's services. Based on the likelihood of abandonment, the user interaction contextualization system may initiate one or more user recapture solutions.