This article is based on a current study which aims to investigate the difficulties translation graduate students from the Arab American University Palestine encounter in translating cultural ironic expressions from Arabic into English. To achieve the purpose of the study, a number of Arab cultural ironic expressions were put in contexts and presented to fifteen translation graduate students to translate them into English. Using a qualitative analytical approach, Gaber (2005) and Newmark (1988) models are employed to identify the difficulties and strategies in rendering Arabic cultural ironic expressions into English by translation graduate students. The analysis of the translations, provided by the students, points out that there are inaccuracies in the translations by the students. Such inaccuracies are mostly due to misunderstanding of the cultural ironic expressions. Misunderstanding is attributed to unfamiliarity and illiteracy in the cultural background of the ironic expressions and the social situations in which they are located. Also, the analysis indicates that the English language proficiency of the students is below average. This is obvious in the poor constructions of the English sentences which they presented. The majority of the graduate students opted for the formal equivalence. Therefore, they provided unacceptable literal translations. The study found that the translation strategies of cultural approximation and functional equivalence can be helpful in achieving a better translation for cultural ironic expressions from Arabic into English.