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Thesis: S.M. in Engineering and Management, Massachusetts Institute of Technology, Engineering Systems Division, System Design and Management Program, 2013.Cataloged from PDF version of thesis.Includes bibliographical references.The benefits of Cloud are quite well known and many companies are trying to harness its potential. They are doing so to increase productivity, deploy newer applications fast, reduce upfront costs and optimize resource utilization. However, some companies are still trying to realize its full potential while dealing with technical challenges such as legacy systems, complexities of integration and other operational implications. The goal of this thesis is to identify the top benefits that companies are gaining through Cloud adoption and the main challenges they are facing in light of this transition. Much has already been written and discussed about these issues in literature. This thesis attempts to seek answers by directly reaching out to top executives of companies to gain real insights and understand the management strategies and best practices that are enabling this transition. By comparing reviewed literature and information gathered through interview analyses, this thesis brings clarity to areas of overlap and the major issues in Cloud computing that were not emphasized or as clearly evident in the literature. Based on the findings, key recommendations are made to help companies effectively transition into the Cloud.