Throughout Rabbinic Literature and Responsa, Jewish texts have clearly privileged speaking the truth over propagating false information, with certain fascinating exceptions. There are definite examples where the truth must be shaped or altered in its presentation for various reasons. Philosophical texts, likewise, sometimes require lies when the truth may cause certain or potential damage. This session will explore a few of the core texts that define this conundrum in Jewish thought, along with a few philosophical responses, sketching the boundaries of shaping the truth and providing guidance for reacting to untruths we encounter. It is not entirely impossible that this discussion will be relevant to contemporary politics and situations that take place in congregational settings.