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This paper explores the conditions and theoretical issues of literary trans-lation, with specific reference to an assessment project of English literaryclassics in translation. It consists of three parts: the internal and exter-nal conditions of literary translation in Korea, a brief report of the projectand its findings with reference to the translations of Pride and Prejudice,and lastly, some theoretical issues involved in such an assessment. Translation has been a significant factor in the formation of mod-ern Korea. However, the conditions of translation and the general qual-ity of translated texts still leaves much room for improvement. Thepractical purport of the project is to identify recommendable transla-tions of English classic novels, but in the case of the 34 translated ver-sions of Austens text, no single recommendable text was to be found.Such a result shows that the quality issue is still crucial, at least in thecontext of Korean translation, in spite of the paradigm shift we are wit-nessing now in Translation Studies from an evaluative approach to adescriptive one. This paper ends by reflecting on the categories of evalu-ation and faithfulness in terms of their theoretical and practical impli-cations.