Deuteronomy imagines a day when, after harrowing exile, Israel will repent and be reconciled with God. Commenting on what he takes to be the text’s insistence that teshuvah (repentance) is accessible and close at hand, one Jewish philosopher lauds repentance for its “ease.” Yet for many of us, the very opposite seems to be the case: We experience real repentance as difficult and demanding, and sometimes even grueling. As Rosh Ha-Shanah approaches, it behooves us to ask just why this might be the case.