Background <p>Learning clinical skills is the backbone of graduate medical education. The present study investigates the learning experience and the enablers and challenges associated with workplace-based learning among oral and maxillofacial surgery residents in Pakistan.</p> Methods <p>An audio-diary based, qualitative case study was conducted among postgraduate residents (both male and female) of oral and maxillofacial surgery (n = 11) from Pakistan. Each participant provided 3 reflective audio diaries (total 33) which were subsequently transcribed and thematically analysed.</p> Results <p>The findings of the study demonstrated that learning in the workplace is multifaceted process shaped manily by clinical exposure, collaboration and supportive organisational environment. Work environment, supervisor and peer support, and availability of learning resources and staff were the key enablers for while excessive workload, lack of support staff and fear of unexpected outcome were the most common barriers to workplace-based learning.</p> Conclusions <p>Understanding the workplace-based learning process and associated enablers and challenges may help organisations running postgraduate residency programs in OMFS to design a supportive and structural clinical training program and enhance learning experience of the trainees.</p>