Chronic condition self-management and lifestyle risk modification education is paramount for General Practice registrars. A multi-dimensional learning package ‘Better Knowledge, Better Health’ was developed and piloted to improve General Practice registrars’ understanding of their role in supporting chronic condition self-management in patients with osteoarthritis. This pilot study was supported by the Australian Better Health Initiative. Pre-training learning needs analysis with a new intake of General Practice registrars (n = 40) indicated high levels of confidence in supporting patients in chronic condition management and lifestyle risk modification, and locating and interacting with local resources and allied health professionals. Conversely, interviews with General Practice Supervisors (n = 13) found most would not identify chronic condition self-management skills as priorities for registrar learning. Supervisors were also not familiar with core principles of chronic condition self-management, in particular application of motivational interviewing to behaviour change. Disparities between General Practice Supervisors’ perceptions of the importance of chronic condition self-management and lifestyle risk modification education and levels of access to learning opportunities in chronic condition self-management for registrars are discussed. Difficulties in implementing a pilot study within tight timeframes are also explored.