This paper investigates the textual relationships between the original English editions of John Bunyan’s novel The Pilgrim’s Progress and its two 19th century translations in their historical context within the late Ottoman Empire. Քրիստիանոսին Ճամբորդութիինը, Աս Աշխարհէս Հանդերձեալ Աշխարհը, Երազի Ձեիով (Kristianosin Cambordutsyunı, As Aşhares Handertsyal Aşharı, Yerazi Zevov) is published in 1843 in İzmir by Gulielmos Griffit. In 1864, roughly two decades later, an Armeno-Turkish translation of the same work appears in İstanbul, printed by Harutyun Minasyan, titled Քրիսթիանըն Եօլճոիլոիղոի, Պոի Տիինեատան Կէլէճէք Տիինեայա, Րիիյա Շէքլինտէ Եափըլմըշ (Kristianın Yolculuğu, Bu Dünyadan Gelecek Dünyaya, Rüya Şeklinde Yazılmış). At a time when private schools start proliferating in Istanbul and elsewhere throughout the Ottoman Empire especially within the Greek and Armenian communities, often in competition with missionary schools, the education of the youth is heavily influenced by what gets published (including what gets translated) and how they are presented. The very choice of translating Pilgrim’s Progress will be contextualized in this paper regarding the missionary education of the Ottoman non-Muslims and the political developments of the era such as the recognition of Catholic (1803) and Protestant (1857) millets in the Ottoman Empire and the drafting of the Armenian Constitution of 1863 for the Ottoman Armenians. A close reading of these two anonymous translations and comparing them to the original English editions of the period might help us better understand the microcosm of the Ottoman Armenian readerships within their larger environment. First, this is an attempt to establish whether the Armeno-Turkish translation is based the Armenian translation or not, and thus understand in the future whether there exist translation trends within the Armenian community in terms of language directionality. Second, comparing the footnotes and editorial annotations in the translations and in four specific original English editions , this investigation aims to reveal whether the anonymous translators insert additional notes and actively contribute to the local reception of the text, and thus start sketching a translational/editorial profile. Third, comparing the translations of Biblical references to some of the available Bible translations of the period in book format, the paper speculates whether translators operate with an awareness of the larger translated corpus of their time by using those existing Bible translations in their own Bunyan translation. How Jesus is made to speak in these translations, i.e. translation strategies, will further suggest their intended and imagined readerships.