During the COVID-19 pandemic, the availability of online higher education programs and tools has grown rapidly. One example is an individual digital study assistant (IDSA) for students, which provides functionalities to train self-regulation skills, to engage with own educational goals and to offer automated, first-level support to higher education institution (HEI) units and employees. An IDSA further can guide students through HEI and their administration. But, what are the critical success factors (CSF) and challenges for an IDSA? We deduce these using a mixed methods approach with one quantitative student survey, two rounds of interviews with various HEI experts, and a literature review. We classified our results according to the information system (IS) success model of DeLone & McLean (2016). Our results and findings show, e.g., that skilled and reliable HEI personnel, well-organized and useful content, cross-platform usability, ease of use, and students’ social factors are essential. Attractive IDSA functionalities are a major challenge because students use many apps, daily. Based on our CSF and challenges, we deduce theoretical and practical recommendations and develop a further research agenda.