The paper discusses the status of shall in today’s legal drafting and legal translation, and by presenting typologies by a number of authors briefly addresses the variety of meanings it is used to express, in both legislation and contracts. It introduces the “shall dilemma” faced by non-native legal translators working both from and into English. The dilemma consists in the discrepancy between the promiscuous and abundant use of shall in authentic as well as translated documents, on the one hand, and the recommendations found in various drafting manuals promoting either a shall-free policy or a disciplined use of shall, on the other hand. The research part presents the results of a survey carried out among a carefully chosen sample of professional legal translators to determine what their policy is on the use of shall. The results include both quantitative findings and additional comments made by the translators, and confirms the divide between actual practice and the recommendations. In the next section of the paper, the results are applied and a series of step-by-step exercises are introduced which should raise the awareness of legal translation trainees of the ambiguity of shall and teach them to use it in a reasoned and disciplined way.