Users can participate in various different types of online sessions, such as webinars, massive open online courses (MOOCs), social learning sessions, and so forth. A record of interactions that the user has with an online session is maintained. During the online session, the user may become disengaged from the online session for various reasons, such as the user losing interest in the information being presented, the user becoming sidetracked due to other programs running on his or her computer or phone, and so forth. The techniques discussed herein detect that a user is not engaged in the online session and generate dynamic content to attempt to re-engage the user in the online session. This dynamic content is personalized to the user, and is based on the maintained record of user interactions with the online session.