This paper addresses the question of normativity in Hegel by examining the role of "undialectical' resistance to dialectical development. Beginning with a general overview of dialectical normativity and what it might mean to be "undialectical,' the focus then shifts to a privileged example in Hegel's writings: Sophocles' Antigone. The central claim of the paper is the following: The very contradictions that fuel dialectical normativity can also trap individuals within an obsolete actuality, without immediate hope of escape. Indeed, the irreducible dependence of dialectical thinking upon the actions and decisions of individual consciousness expose it to the threat of continual stasis or regression. This ineliminable possibility of failure is what is here called the "undialectical' moment of the dialectic, which Hegel understands rather as a negative condition of possibility of freedom and rationality.