Workplaces are complex, dynamic spaces. While some practices are routine and highly predictable, informed by disciplinary and practical knowledge, others are unpredictable and emergent. Outcomes-based education, characterised by standardised, objective measurement of performance under controlled conditions, might be appropriate for routinised practice, but cannot account for emergent forms of professional knowledge. Somewhere between developing pre-specified, discipline-based skills and knowledge, and adapting to situated, contextualised conditions, there must be a capacity for dynamically developing unpredictable practices. This, we argue, should be an important focus of professional education across academic and practice settings. We interviewed 14 teachers and professionals studying part-time, across a range of disciplines, including medicine, architecture, law and allied health professions, about the alignment of learning within the workplace and university assessment. Using a sociomaterial lens, we offer a seamful account of educational and professional settings, manifested through assessment, regulatory bodies, technology and materials. Each seam represents ways of patching contexts together (e.g. accreditation stitches requirements of professional practice into educational approaches). Exposing such seams can reveal limitations and possibilities of classrooms and workplaces as sites of professional learning, whereas hiding the complexity of professional practice may be counterproductive to developing students' adaptive capacity to successfully negotiate practice settings.