Use of digital resources to facilitate work-based learning and assessment tasks has become an increasing priority for implementation of curricula in clinical workplaces. This year the medicine program at Monash introduced the use of PepplePad as a platform to provide an ePortfolio to collect work-based assessment completed by students in their first clinical year (Year 3 of the course). This year approximately 400 students located across several clinical sites have been completing ePortfolios for work-based assessment tasks. This required translation of existing assessment tools into the ePortfolio as well as navigating implementation and user issues. Communication with and training for staff and students across multiple locations has been complex and differing attitudes and expectations across stakeholder groups has been evident. Introduction of this initiative has created some challenges but has also provided benefits in terms of monitoring and recording student performance of assessment tasks.