Abstract: Motivated by applications in electronic games as well as teaching systems, we investigate the problem of dynamic difficulty adjustment. The task here is to repeatedly find a game difficulty setting that is neither `too easy' and bores the player, nor `too difficult' and overburdens the player. The contributions of this paper are ($i$) formulation of difficulty adjustment as an online learning problem on partially ordered sets, ($ii$) an exponential update algorithm for dynamic difficulty adjustment, ($iii$) a bound on the number of wrong difficulty settings relative to the best static setting chosen in hindsight, and ($iv$) an empirical investigation of the algorithm when playing against adversaries.