This paper charts the clinical course of a serious impasse and its resolution in the psychoanalysis of an obsessional patient. During the impasse, traumatic, unconscious conflicts activated via the transference/counter-transference matrix, precipitated the emergence of psychotic phenomena in an otherwise non-psychotic individual. That we all live on the edge of madness is a truism and actual states of madness can emerge with dramatic force within the crucible of severe transference/counter-transference struggles. Such episodes of unexpected psychotic experience require the analyst fluidly and flexibly to modify technique. Willingness to engage in symbolic enactment, the creation of transitional space, and other forms of active, spontaneous engagement with the fabric of madness become necessary in order creatively to respond to the collapse of normative symbolic, therapeutic exchange.