Surgeons require advanced psychomotor skills, critical decision-making and teamwork skills. Much of surgical skills training involve progressive trainee participation in supervised operations where case variability, operating team interaction and environment affect learning, while surgical teachers face the key challenge of ensuring patient safety. Using a theoretical framework of "situated learning" including "cognitive apprenticeship," we explored teachers' and trainees' beliefs and values about intra-operative training and reasons for any differences. A qualitative case study method was used where five teacher-trainee pairs participating in an observed teaching operation were separately interviewed about the same operation. Thematic analysis of transcribed interviews and observations was performed with iterative refinement and a reflexive approach was adopted throughout the study. We found that in all cases, teachers and trainees had shared recognition of learning about technical skills whereas they differed in three cases regarding non-technical skills such as surgical reasoning and team management. Factors contributing to teacher and trainee satisfaction with the process were successful trainee completion of operation without need for surgeon take-over, a positive learning environment and learning new things. Teaching--learning behaviours observed and discussed were modeling, coaching and scaffolding, while exploration, reflection and articulation were less common. Our study reveals differing teacher and trainee perspectives of some aspects of intra-operative training and surfaces new reasons other than amount of feedback and autonomy given. Factors contributing to different perspectives include teacher and trainee abilities, values and situational influences. Targeted teaching--learning strategies could enhance intra-operative learning.