The main objective for this thesis is to identify a set of challenges imposed on an organization undergoing strategic change impacting their IT Landscape. Organizations most embark on strategic change initiatives in order to remain competitive and create business value. It is important to understand these challenges imposed during the change process in order to be prepared and able to minimize the negative impact they may have if not handle properly. For this purpose within the scope of this thesis the aim is to identify challenge areas and the specific challenges they may impose. These identified challenges can be used as a baseline for organizations in order to understand which areas to address in order to minimize negative impact during a strategic change related to their IT Landscape. A case study methodology was used in this thesis and relevant research through literature review in identified topics was conducted. Communication, leadership, business value and strategy realization, knowledge management and change management are examined through the theoretical framework and identified as areas in need of attention during a strategic change initiative. Also within the theoretical framework this thesis identifies Enterprise Architecture as an enabler for succeeding with the change initiative related to the IT Landscape. The qualitative empirical data for this thesis was collected through the interview of ten professionals within four different organizations. Based on the above approach, within the scope for this thesis, a set of challenge areas and specific challenges were identified and the conclusion was that these areas are important to address during a strategic change initiative impacting IT Landscape within an organization in order to ensure a successful outcome.