This paper explores Ghana’s two-decade journey in developing a digital land information system (LIS), exemplified by Ghana Enterprise Land Information System (GELIS) and Enterprise Land Information System (ELIS). Despite advancements by Ghana’s Lands Commission, manual processes persist and coexist with digital ones. Our study uses a qualitative approach to assess the effectiveness of the LIS implemented in Accra. This study found that Accra’s LIS is highly aligned with clear institutional mandates, roles, and responsibilities, as well as the availability of laws and policies to support analogue-to-digital conversion. Furthermore, a robust approach to protecting the data, operating system, and software underpins the system. Subsequently, the integration of a digital LIS has enhanced service delivery and accountability. Nonetheless, Accra’s LIS is still at the beginning of a comprehensive learning and development curve. Sustaining the LIS requires furtherance in the implementation plan, funding, law implementation, ICT strategy, divisional integration, work processes, data quality, and communication strategy. These findings will inform the next steps of improvement for Accra’s LIS and guide its nationwide scaling, contributing to discussions on technology acceptance dynamics in predominantly analogue environments.