Medical terminology represents a historically rich and highly systematized domain of specialized language, shaped by the enduring influence of Greek and Latin as well as by contemporary English-dominated scientific discourse. This article examines the translatability of medical terminology from English into Greek through four complementary dimensions: linguistic, conceptual, cultural, and technological. Drawing on terminology theory, translation studies, and corpus-based approaches, the analysis highlights the morphological asymmetries between English and Greek, the semantic divergences that challenge strict term-to-term correspondences, and the cultural-ethical nuances embedded in concepts such as informed consent and palliative care. Special attention is given to the phenomenon of “reverse translation,” in which English medical terms of Greek etymology acquire new meanings that do not always align with their historical roots. The study also evaluates the role and limitations of contemporary translation technologies—terminology databases, Computer-Assisted Translation (CAT) tools, neural machine translation, and Artificial Intelligence (AI)-driven semantic systems—particularly in relation to Greek, a language underrepresented in multilingual biomedical resources. The article proposes a context-sensitive model of medical translation that integrates linguistic expertise, conceptual knowledge, cultural mediation, and critical technological literacy. The findings underscore the translator’s role as a terminological curator and interdisciplinary mediator, essential for ensuring precision, consistency, and cultural relevance in Greek medical terminology within a globalized scientific environment.