Modern Jewish prayer books face an intractable dilemma: how to serve both congregational worship and private devotion while confronting declining prayer frequency and varying Hebrew literacy among American Jews. Three prominent rabbis - David de Sola Pool, Ben Zion Bokser, and Gershon Hadas - attempted to resolve this challenge through distinct approaches in their recent prayer book editions. Through comparative textual analysis of translation methods, arrangements, and accessibility features, clear patterns emerge in how each edition navigates between tradition and modernity. Pool's Orthodox edition maintains Victorian English dignity but encountered theological authorization challenges. Bokser achieves a more successful balance by employing modern language while preserving traditional "thou" forms for divine address and emphasizing God's mercy through interpretive translation. Though aiming for colloquial simplicity, Hadas's Conservative movement edition is hampered by problematic organization and a responsive reading format that assumes substantial Hebrew knowledge. While all three editions attempt to bridge traditional liturgy with contemporary needs, none fully reconciles the competing demands of accessibility, theological authenticity, and practical usability. These translation challenges reflect deeper tensions between historical Jewish tradition and modern American Jewish religious practice, suggesting that effective liturgical renewal requires addressing fundamental questions of faith and communal worship beyond mere textual revision.