Cloud Outsourcing (CO) is a new form of outsourcing which is to yet to be implemented. Unlike traditional Outsourcing, CO is a form of outsourcing in which software organization outsource the work to e-freelancers available throughout the world using cloud services on the Internet. In this guide we have narrated how the process of CO is carried out internally in organizations. Some internals of CO such as sequence of activities involved during the entire process of CO, the risks which are likely to be occurred during the implementation of this process, prioritization of the elicitated risks according to their probability of occurrence, impact and cost required to mitigate the corresponding risk are clearly explained with support of literature, professionals' experiences and global survey. This guide also presents the synthesized recommendations, precautions and a checklist which are required to be considered whenever an organization wants to step into CO. Research gaps in CO are also mentioned in this guide which needs further exploration.