While the Hebrew word ָא ֵמן and its transliterated borrowing into Greek ἀμήν in the New Testament epistles generally signal agreement at the end of a prayer, doxology, or blessing, the “Amen (Amen), I say to you” formula in the gospels (with the repeated “amen” only in John) occurs clause-initially and serves to introduce certain direct quotes of our Savior. In the first part of this paper, we seek to confirm Clark’s 2004 and 2007 observations on the discourse and pragmatic functions of the “amen” formula signaling the beginning, end, and high points of a literary unit. We go on to complement these findings by noting that in the Gospel of John, the formula can also announce a coming theme, mark a climax, conclude a larger discourse unit, and occur in clusters, moving from neutral to more conflictual contexts. In the second part of the paper, we consider translations in a number of versions in English and a set of African languages, examining translation strategies which include more literal and more dynamic renderings. We ask if it is better to translate or transliterate the “amen” formula, render it consistently or not, and preserve the repetition of the formula in John’s Gospel. In at least some languages, insistence on the truth of a statement may indeed raise doubts as to its credibility. This study underlines the unending tension in translation between form and meaning, but also brings to light how John’s quotation of this Hebrew and/or Aramaic expression within a Greek text lends authenticity to this gospel. Finally, our observations lead us to ask: Is it time for translators to imitate the gospel writers’ attempts at preserving the flavor of Jesus’s speech in the gospels by opting for transliteration rather than translation?