Higher education institutions are increasingly looking to the cloud to migrate legacy applications from their local data centers. This transition promises numerous benefits, including ease of maintenance and reduced expenses; however, there are many pitfalls that need to be avoided. This presentation will explore the challenges and opportunities we faced at Florida State University Libraries in moving a complex legacy digital repository system containing almost 40 terabytes of data from on-premises servers into the cloud (AWS). This project presented numerous administrative, technical, and user-focused challenges that we will address in turn. With respect to administration and technical staffing, the project required extensive reskilling and reprioritization of our staff to function as a modern, cloud-forward DevOps team. We spent considerable time breaking down a monolithic software application to take advantage of containerization, flexible storage systems, and improved continuity of operations. We also undertook a change management process to acclimate users to the new system. In addition to greatly improving the performance of our system, this project has also given us much greater control over the customization and development of new functionality, greatly benefiting both our employees and our users. We believe that the lessons we learned over the course of the project will also benefit IT professionals looking to undertake similar projects at their institutions.