Physician health is a global concern, with increasing research efforts directed towards the challenge. Australia has limited published specialty-specific well-being data for trainees and consultants in medicine and surgery. We measured distress in Australian Orthopaedic trainees using the Physician Well-Being Index (PWBI, MedEd Web Solutions) using an online anonymous survey sent by the Australian Orthopaedic Association. The survey response rate was 38% (88/230). Forty-four percent of survey respondents met criteria for distress. Self-reported burnout in the 30 days prior was reported by 63% of respondents. Fifty-eight percent of females and 41% of males met criteria for distress. Of the 19% or respondents identifying as an ethnic minority, 53% were distressed compared to 42% of those identifying as non-ethnic minority. Trainees without a mentor had a 50% distress rate compared to those with a mentor (37% distress rate). Twenty-five percent of all trainees wished they had picked a career outside of medicine and 16% wished they had pursued a medical career other than Orthopaedic Surgery. Of those trainees who had already passed the fellowship exam, 17% wished they had pursued a career outside of medicine and 21% wished they had pursued a medical career in an area other than Orthopaedic Surgery. These findings suggest concerning rates of career regret and gender-related trends in distress in Australian Orthopaedic trainees. Females may be over-represented in our results as 17% of the source population was female compared to 22% of respondents. Further research is required across all Australian specialties to gain further understanding of factors contributing to distress and to assist in the development of strategy to protect against physician burnout.