The aim of this study was to investigate the benefits and challenges of moving information systems to the cloud infrastructure as part of phasing out legacy systems and preventing digital fraud. This study employed a qualitative research methodology and used interviews, observations and document analysis as data collection methods. It was confined to one bank and is therefore classified as a case study. To protect the identity of this organisation, the researcher gave it a pseudonym called SA Retail Bank. The study yielded three major findings. Migration of applications to a cloud environment is characterised by several unexpected technical, regulatory and people challenges. However, the migration yields operational benefits such as reducing fraud, quick recovering of stolen moneys, and advancing Fourth Industrial Revolution technologies. Technology acceptance theories should also be prioritised to get the support of both internal users and customers. The findings of this study present important lessons for digital businesses in South Africa and abroad. The research yielded theoretical and practical contributions. Recommendations were also made for future research.