Digital transformation in Higher Education and Science is a mission-critical demand to prepare educational institutions for their future competition on the international market. In many cases, the digitization goes along with the search for and acquisition of new software. For easily exchangeable software, wrong product decisions, in the worst case, lead to calculable financial losses. However, if a planned software requires a lot of technological adjustments and is to be applied as central component of a business-and/or security-critical environment, wrong decisions during the software acquisition process might lead to hardly calculable damage. Questions arising are how to decide for a product and how many resources should be invested for the acquisition process. We planned to apply a commercial Business Support System, which should replace the currently used in-house developed software. Our goals were the increase of our university's level of data security, to ease the interaction between stakeholders, to eliminate media discontinuities, to improve the process management and transparency, and to reduce the execution time of automated processes. Alongside with the introduction of the electronic case file, our agenda stipulates the digitization (and automation) of administrative university processes, especially, but not limited to, the student self-service and the administrative student life cycle. Usual tools and practices, commonly applied to (simple) software acquisition, failed in our scenario. With the case study introduced in this paper, we address all persons, involved within software acquisition processes: From our experiences, we strongly recommend to place greater value on an exhaustively completed acquisition process, than on short-termed economic advantages.