Abstract: Translation theory, although a young science, has deep roots dating back centuries, with the dichotomy between literal and free translation evident since the time of St. Jerome. This paper examines the evolution of this basic translational dichotomy across different theoretical frameworks, including formal equivalence, dynamic equivalence, communicative and semantic translation, foreignization, domestication, etc. The authors also highlight the differences between the theoretical concepts. Furthermore, the paper focuses on how the translation dichotomies may be applied in practice. To this end, the study delves into how the dichotomy manifests in student English-Russian translations, specifically focusing on achieving functional equivalence. The point of departure for the analysis is J. Houses’s definition of covert translation. Analyzing translations of a scientific text by first-year master's students, the paper reveals challenges in achieving covert translation. The methods employed in the paper are the following: a componential analysis; a translation analysis, a corpus-based analysis; literature review, and retrospection and interviews. Scientific novelty is related to the application of basic theoretical concepts in practice, namely, in the practice of teaching translation. Moreover, the paper provides a comprehensive overview of existing theoretical approaches to describe the opposing translation strategies: word-for-word and sense-for-sense translation. In addition, the authors argue that translation errors are caused by an incorrect approach to the translation process itself. The interviews revealed that students often view translation as a replacement of source text units with translated text units, ignoring the overall translation strategy. The results highlight recurring collocational errors, indicating a source language-dependent tendency. The conclusion emphasizes the need for a pedagogical shift toward functional perspectives in translation training, suggesting avenues for future research on translator training.