This dissertation aims to assist Agile champions in their organisations with their Agile adoption journey. Such a journey typically starts with identifying the Agile challenges and then determining how to address these challenges in their unique context (Hajjdiab & Taleb, 2011a:9). This study provides a manual together with an automated framework to showcase a list of prioritised Agile challenges and their corresponding possible solutions. Before reaching this automated framework, the research presented a comprehensive list of Agile adoption challenges, possible solutions and a mapping between them. The automated framework, also named Agile Adoption Coach (AAC), is in the form of an online tool: www.agilesense.coza/aac. The critical quantitative contribution to this study was the evaluation of the AAC by Scrum Masters and Agile coaches to determine the acceptability of the tool. The research has shown that there is, on average, an 86% acceptability rating for this tool in South Africa. / School of Computing / M. Sc. (Computing)