There is much literature on the challenges of designing for and implementing ePortfolios. Issues include technology management and overcoming barriers to acceptance and usability. Yet as higher education practitioners we find ourselves continually stumbling over these issues. Through discussion of a work-in progress case study at a large Australian medical school, we raise some of the design and implementation issues that impacted integration and facilitation of an ePortfolio system. The system

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... was created to support students' personal learning, and evidencing and assessment of clinical competence. Recognising the importance of context, we focus on a Workplace Learning Portfolio (WLP) course, in which an ePortfolio system was adopted to support and deliver workplace-based assessments for students in Years 3 and 4 of a Doctor of Medicine (MD) program. Discussion centres around the promise and reality of concurrently implementing curriculum and technological change with a large cohort of domestic and international students. The complexity of using an ePortfolio system to identify students at risk of academic failure is raised, as is an example of unexpected student engagement with personalised learning.