This article draws on Winnicott's concept of the good enough mother to discuss how to know whether a therapeutic situation is good enough to continue or bad enough to end. This dilemma is explored in terms of clinical syndromes, such as anorexia and pathological gambling, but focuses mainly on analyst-initiated endings, which are termed the ‘Casablanca dilemma’, based on an amplification of the ending of the film Casablanca. The author goes on to discuss such one-sided endings, drawing on interviews with 40 analysts and therapists about their clinical experience. A typology of bad enough endings is presented. The psychological differences between a good enough analysis as opposed to a bad enough one are explored through the ideas of Winnicott and Neumann.