This paper investigates translation problems and obstacles in the translation of ITtexts from English into Arabic. It explores the numerous challenges and issues that professional IT translators face in dealing with localizing ITprojects. Considering that localization is an activity constrained by limitations of time, process, and cost, IT translators need to make use of their entire skillset to overcome the varied challenges imposed by the source text and the localization process itself. The present paper provides a ranked classification of problems in translating from English into Arabic through browsing some unique and important web applications such as Oracle, Microsoft, Google, and SAP systems. The paper concentrates on the causes that lead to such issues and problems and provides the possible and available solutions to avoid such problems. This paper aims to analyze and identify the functional approaches in translating technical ITterms, focusing on the main issues that face IT technical translators.The current paper follows Skopos methodology, which takes into account the cultural and environmental standards when transferring the translated text from English into Arabic, thus the technical translator must be highly conversant and have extensive experience with the culture and environment in which the translated text will be marketed. It also cares about the constraints and obstacles of the Arabic language systems and dimensions and how to avoid them in combining English terms within Arabic translated text. Finally, the paper focuses on the identification and categorization of problems of localization of online help files for web applications. Online help is a digital product that offers assistance to the user to carry out tasks in a specific application or that answers questions about specific aspects of the interface of the application, its operation, or its characteristics. The central question of this paper covers broadly the kinds of problems that a translator faces in the localization process of online help.