In this paper I intend to explore the challenges that literary translations might experience following the advent of online translation software (such as MemoQ) and will discuss the advantages/disadvantages of using such software in the translation of different types of literary texts. In my research I shall demonstrate that the use of MemoQ in the case of literary texts is ambiguous: while it can be useful for translating even literary texts, the quality of such translations differs from one text type to another.