The late antique rabbis of Roman Palestine were seasoned jurists, experts on exegesis and legal interpretation. Yet rabbinic literature does not theorize. A positive account of rabbinic conceptions of language therefore remains a desideratum. I choose an alternative approach. Legal reasoning relies on language to ground the determinacy of the law. Jurists must thus confront language when it threatens to undermine the latter. Conversely, they may hold language to safeguard legal determinacy. Drawing on insights from legal theory, I turn to an unusual rabbinic rule of inference. Its earliest attested version suggests a universal possibility of inference “from the category of yes that of no, from the category of no that of yes.” I show that the ever-evolving uses of this rule allow us to observe a shift in linguistic attitude, increasingly acknowledging linguistic uncertainty. My findings tie in with recent advances in the study of rabbinic exegesis.