This paper presents a practitioner's view on student system implementations in the Australian university sector. A student information system is a core system of any university and integral to its operations and services to students. These systems are constantly on the list of major projects and at any point in time, a university is either implementing a new system or upgrading an existing one, or planning for either or both. These projects are costly, time-consuming and share common challenges that can be attributed to a combination of factors including software implementations, peculiarities of the individual institution, the sector, the software supplier and the environment in which it operates. Themes underpinning these challenges are explored and discussed with a view to creating greater understanding of the many facets that come into play. Questions are posed on future needs and directions given the challenges ahead, particularly the major sector reforms.