Background and Purpose: This paper presents findings from a study which aimed to explore contextual, personal and professional factors in applying training in the use of a new stroke self-management programme. Methods: Practitioners completed in-depth case reflections as part of their two-day training in the Bridges stroke self-management programme (SSMP). The study utilized a qualitative approach to explore the understanding and meaning participants gave to their experiences of using the SSMP. Data from case reflections were analysed using a thematic content analysis. Results: Data from 60 case reflections were included in the analysis. Several themes were prominent including: timing, belief in the concept of self-management, congruence with goal setting, balance of power and subtleties and sensitivities of using the SSMP. The use of in-depth case reflections enabled a personal awareness of the complexities of supporting self-management after stroke. Participants reflected on their communication styles and interactions and how they influence the development of self-management skills in individuals post-stroke. Conclusion: Case reflections offered an opportunity for participants who had received training in the use of an SSMP to explore their experiences of using the programme with individuals post-stroke. This enabled personal reflection on learning and facilitated a wider discussion on the professional and organizational context concerning integration of a self-management programme into stroke rehabilitation. The paradox between professionals having a role as 'experts' and the subtle changes in practice towards a more collaborative therapeutic relationship to support self-management needs further exploration. Implication for practice: Physiotherapists were required to make a change in their practice from traditional, educational, hands on approaches to one which gave more prominence to facilitating an individual's problem solving, collaborative goal setting and decision-making post-stroke. This study highlights a number of issues relevant to professional learning and education in respect of self-management.