The haunting melody of Kol Nidrei stands as one of Judaism's most beloved prayers, yet it harbors a deep paradox: a legally problematic formula that has drawn sustained rabbinic criticism throughout history. From its origins as a mechanism for annulling vows to its current liturgical form, Kol Nidrei's evolution reflects a fundamental tension between legal precision and spiritual resonance. Through historical analysis of sources from the Tanakh through the Geonic period, Diamond traces how various textual formulations emerged while documenting persistent opposition to its improper structure and potential to mislead congregants about vow annulment. Despite its legal inadequacies and self-contradictory nature in most contemporary versions, Kol Nidrei functions as a meditation on the "promise and problem of words" that addresses the post-Temple theological crisis. The prayer emerges as one of four key liturgical responses to the loss of concrete Temple ritual, alongside the Avodah service, martyrology, and invocation of divine attributes. Kol Nidrei's unique power lies in its simultaneous affirmation and critique of language's performative potential, serving as a reminder that verbal commitments must be matched by actions—a duality that makes it particularly fitting for opening Yom Kippur, when transformation through repentance and the alignment of words with deeds take center stage.