The Digital Transformation phenomenon always tends to be complicated, ambiguous, challenging, and non-routine managerial tasks for organizations. The success rate of such digital transformation is very low due to rapid changes in technologies. Digital transformation through these technologies demands a fundamental change in organization processes, technology and behavior of the people. This broad change results in different socio-technical issues and challenges. The primary objective of the study is to discover issues, challenges and impact/benefits during digital transformation, investigated by various researchers. For this purpose, a systematic literature review (SLR) as prescribed by Levy and Ellis (2005) helped in identifying the challenges of digital transformation. The articles published from 2008 to 2018 were selected and analyzed. The findings of this research reflect the importance of developing an effective digital transformation strategy in organizations. The proactive strategy regarding people, process, technology, and most importantly their alignment in the organization is found critical in executing such transformation initiative in the organization. The planned efforts regarding knowledge management also played an important role in executing and sustaining such transformation initiatives in the organizations. Moreover, value creation, operational efficiency, competitive advantage, customer relationship, and new business model emerged as a vital motivational factor and outcome for digital transformation. Keywords: Digital transformation, digital transformation issues and challenges, systematic literature review, digital transformation benefits/impact.