The convergence of cloud computing, mobile technology and big data technologies is transforming information technology faster than ever before. While there is an established knowledge base of known implementation issues relating to project management, technology, user resistance, organisation/environment and outsourcing, digital technologies introduce new challenges. This chapter summarises traditional challenges in information system implementation and discusses some of the issues arising from the deployment of digital technologies including migration to the cloud, security, data protection and information and communication technologies governance, contractual issues in the cloud, big data and mobility.