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This paper examines the extensive use of litigation by merchants of Jewish origin plying the sugar trade route – Brazil, Portugal and the Netherlands – in the late sixteenth and early seventeenth century. It argues that the legal system was not only a feasible remedy but actively used to solve commercial disputes among traders of various origins across wide distance and different political units, even during wartime. Litigation was also frequent amid within the Western Sephardic and converso tradesmen, which allegedly constituted a closely-knit trading diaspora. In fact, formal coercion coevolved and interplayed with the informal mechanism for securing compliance with mercantile norms and agreements rather than competed with them for prevalence. When the informal mechanisms failed, merchants turned to the more costly, slower and doubtful legal verification and enforcement. To better count on such a resolution, merchants produced official documents, which functioned like an option in nowadays business: their costs were all the more sensible the more the parties feared to have to resort to litigation later on. Both authorities and merchants enhanced the effectiveness of the legal system by establishing a growing standardization, universalization and enforceability of trading customs and routines throughout Europe and its colonies. Furthermore, private documents produced in such routines were increasingly admitted as evidence in court, sometimes in summary procedures and at specialized mercantile tribunals. Authorities also recognized the legal tender of both official and private documents produced abroad. Trade expansion both engendered and was enhanced by this process.