Even in routine analytic work, for what is dissociated to become symbolized and available to conflict resolution, a patient must experience sufficient interpersonal safety to free working memory while activation of unprocessed dissociated experience is taking place. The author proposes that this necessary synthesis of affective security and relational risk depends on what a given patient and analyst do in an unanticipated way that is safe but not too safe—an enactment of the relational failures of a patient's past while allowing “safe surprises” in the here-and-now to occur. Remarkable convergence is found between cognitive research (W. Bucci, 2003), neuroscience research (J. E. LeDoux, 2002), and an interpersonal/relational psychoanalytic approach that works at the interface of dissociation and conflict.