The recent years have witnessed an increasing importance of machine translation systems due to the prolific production on online texts in different disciplines and furthermore, the inability of traditional translation methods in addressing translation needs all over the world. It is even argued that training on translation tools should be integrated into translation pedagogies and ultimately, courses should be provided for students and professionals. In spite of the effectiveness of translation tools and systems in providing solutions in relation to different disciplines and text genres, the usability and reliability of such systems in terms of literary texts, however, is still highly controversial. Many critics and educators still underestimate the usefulness of the machine translation systems in literature, which could be partially attributed to the unique nature of the language of the literary texts. The issue has its pedagogical implications to translation instruction due to the needs to integrate emerging technologies in teaching and learning practices. For proper use of translation technologies in educational contexts, these need to be well evaluated. For this purpose, this study evaluates the usefulness of applying machine translation systems to literature with the purpose of identifying the challenges that may have negative impacts on the reliability of machine translation systems. In order to do this this, two translation systems are selected, namely, Google Translate and Q Translate. By way of illustration, the study is based on a corpus of two English short stories. The study is based on two prose fiction texts. The first is J. K. Rowling’s novel Harry Potter and the Philosopher’s Stone. The second is Edgar Allan Poe’s short story The Black Cat. Automatic translations generated by the two machine translation systems were compared to human made Arabic translations with the purpose of identifying the problems within these translations. Results indicate that different lexical, structural, and pragmatic errors are encountered by users which negatively impact the reliability of these translations. Educators and translation instructors need to reflect on the challenges of machine translation systems in relation to literature. Software developers need also to address the problems faced by users and students in the translation from and into the Arabic language.