The present disclosure is directed to interactively counseling a user with respect to supervised content. In particular, the methods and systems of the present disclosure may: determine, based at least in part on one or more machine learning (ML) models, that one or more interfaces displayed to a user include content of a content type designated by a content supervisor of the user for identification; and, responsive to determining that the interface(s) displayed to the user include content of the content type designated for identification, generate data representing a graphical user interface (GUI) for presentation to the user, the GUI indicating detection of the content of the content type and comprising interactive educational material counseling the user with respect to the content type.