The Kerala High Court’s experience in digitisation highlights the complexities of developing technological solutions for courts within a federal structure. The diversity in practices and procedures across different high courts presents a unique challenge for developing a nationwide digital solution. The iterative and stakeholder-inclusive design and implementation process of the CMS is a model to create a system that can accommodate this diversity while unifying administrative and legal processes. The Kerala High Court’s CMS model is a valuable example of how to develop and implement a technological solution that meets the unique needs of courts within a federal structure. It is a model that other courts and students of technology and the legal system can learn from. Our study focuses on three main technology-enabled reforms – (1) e-filing, (2) online scrutiny of pleadings and (3) paperless courts. Our goal is to present a well-rounded and nuanced case study that reflects the diverse experiences of those working within the justice system and to help untangle the inner workings of the registry that is crucial to understanding the scale and requirements of justice reforms.