“If you translate long into the machine, the machine translates back into you,” is one of the issues the present article strives to establish and explore qualitatively. I intend to examine the effectiveness and efficiency of machine-assisted translations of significant literary works from a hermeneutical perspective. Essentially, I analyse the output of automated translation platforms such as Google Translate and compare them to human translation. This investigation is valuable in determining whether translators should exercise caution when utilizing translation platforms for culturally rich literary works. Additionally, the article scrutinizes the localisation, cultural, and grammatical coherence of Homer’s