This disclosure describes methods, non-transitory computer readable storage media, and systems that generate digital content for users to access in a social networking platform and detect user interactions with such digital content as part of user-interaction evaluations to determine the users' digital media literacy. For instance, the disclosed systems receive a request to initiate a user-interaction evaluation in a social networking platform. In response to the request, the disclosed systems generate digital content (e.g., social networking posts from a digital media bot) as part of the user-interaction evaluation for users to access in the social networking platform. The disclosed systems further detect interactions by user accounts with the digital content within the social networking platform and then generate digital-media-proficiency metrics for the users based on the interactions. The disclosed systems accordingly determine digital media proficiency of the users according to the user-interaction evaluations by leveraging targeted digital content.