Digital study assistants (DSA) aim to support the challenging tasks of searching for relevant information and organizing this data for individual study planning. Although such systems are characterized by complex process flows, their user experience (UX) has rarely been examined adequately. This research comprehensively analyzes the UX of such a system at the University of Bamberg, which includes short-term planning for one semester as well as the distinctive feature of long-term planning beyond one semester. Via remote usability testing including an online questionnaire and involving 26 participants, this study explores students’ interactions with the system and evaluates the impact of the system design on the UX, identifying strengths and weaknesses. The study has revealed that participants faced major challenges related to complexnprocesses resulting from the lack of functional and terminological differentiation between short- and long-term study planning for users. In addition, certain features, including extended search options, were hidden and could not be found immediately. Derived from these findings, we present nine design principles to guide the development of effective DSA and similar support systems.