storing data indicative of a user performance level identified based on an analysis of collected game performance data associated with a user exercising a plurality of different skills in a virtual environment of a digital content title;

comparing the user performance level to a specified expectation level associated with each of a plurality of available activities in the digital content title;

predicting one or more deviations between the user performance level and the specified expectation level based on the comparison, the predicted deviations corresponding to one or more upcoming events associated with a set of different skills within a current interactive session;

selecting a game difficulty parameter of a set of game difficulty parameters to apply to each of the upcoming events based on the predicted deviations, wherein the game difficulty parameter is selected based on an ordering of one or more of the different skills associated with the respective upcoming event; and

dynamically applying the selected game difficulty parameter to the associated event of the upcoming events during the interactive session, wherein the user is challenged to exercise the skill from the set associated with the associated event in accordance with the dynamically applied game difficulty parameter.