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When a patient presents for psychotherapy having accessed illegal images of children online, it may be impossible to know at the outset whether this reflects an enduring sexual interest in children, or the transient emergence of paedophilic sexual interest associated with a breakdown in ego functioning. Concerns about risk and the emotive nature of paedophilia may undermine the therapist's or analyst's capacity to tolerate uncertainty and maintain analytic neutrality, leading to premature assumptions about the nature of the underlying pathology. This paper describes the treatment of a patient who had a conviction for viewing indecent images of children online, and the challenge of suspending judgement and maintaining analytic doubt while exploring the meaning of his actions. There was a pressure towards a sadomasochistic transference in which the therapist would be perceived to be cruel if doubting him, but weak and naive if not questioning him. Analytic work over seven years led to a formulation of his acting out as reflecting, not enduring paedophilia, but a ‘paedophilic breakdown’. Changes were evident in his psychic functioning and his external life, as well as in the quality of the therapeutic process. The countertransference challenges of this work are discussed.