This particular study explores and identifies the obstacles faced in the process of translating idioms from the Arabic into the English. In fact, one of the most challenging issues in the field of translation is the process of translating idioms from the source language into the target language with maximum success in conveying similar connotation, conceptualization, as well as shades of meaning. Therefore, in meeting the objectives outlined in this study, a purposive sample that consisted of forty students pursuing B.A. in English at the Arts College of Al Imam AL Mahdi – Sudan had been selected. Other than that, the researcher employed the descriptive approach in the study to identify and to list down the problems faced by students in applying certain strategies to translate idioms from Arabic into English. As such, a translation test was carried out as an instrument for data collection. The test was comprised of twelve Arabic proverbs based on Speake (2008) classification of Proverbs, i.e. everyday experience, traditional wisdom, and folklore, to name a few. As a result, the outcomes of the study revealed several issues that must be ironed out in order to translate idiomatic expressions appropriately and accurately. Some significant factors that had been included are cultural aspects, sociolinguistic elements, linguistic and stylistic considerations and some particular meta-lingual factors.