This chapter analyses a paradox presented by the theory of confidentiality in professional relationships. On the one hand, professionals are universally expected to demonstrate qualities of honesty, truthfulness, and reliability in their dealings with clients, with each other and with the wider public. On the other hand, however, the ethic of professional confidentiality, designed as we have seen ... [Show full abstract] to shelter the privacy and enhance the autonomy of the individual, quite often seems to require professionals to be, at least, economical with the truth, and on occasion even to misrepresent the full truth in order precisely to protect confidentiality. Professionals thus seem to be bound by a double standard of truthfulness, which must be an absurdity. Drawing on recent theorising about truth telling from philosophers MacIntyre and Williams, the chapter proposes that professionals have to operate by a moderated or ‘watchful’ truthfulness, with professional confidentiality as a three-cornered contest of the professional's truthfulness towards the individual client, towards other people proximate to the client, and towards the wider public good. Such a model serves to make the dilemmas that practitioners are expected to resolve on a daily basis while being obligated by unclear and frequently contradictory professional duties, rules, and procedures, better understood.