Systems are provided for providing a contextualized set of help topics. A user interaction contextualization system receives a search request for help topics from a user device, responsive to which the user interaction contextualization system retrieves an uncontextualized set of help topics from a help topics index. 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 generate a contextualized set of help topics.