Introduction: Fostering trainee psychological safety is increasingly being recognised as necessary for effective feedback conversations. Emerging literature has explored psychological safety in peer learning, formal feedback and simulation debrief. Yet, the conditions required for psychologically safe feedback conversations in clinical contexts, and the subsequent effects on feedback, have not been explored. Methods: We conducted a qualitative study using interviews and longitudinal audio-diaries with 12 rural general practice trainees. The data were analysed using framework thematic analysis to identify factors across the data and as individual participant case studies with illustrative vignettes of dynamic interleaving of factors in judgements about feedback conversations. Findings: Findings identify the influence of intrapersonal (e.g. confidence and comfort to seek help), interpersonal (e.g. trust and relationship) and sociocultural factors (e.g. living and working in a rural community) that contribute to psychological safety in the context of everyday feedback conversations. Multiple factors interplayed in feedback conversations where registrars could feel safe and unsafe within one location and even at the one time. Discussion: Participants felt psychologically safe to engage their educators in sanctioned systems of conversation related to the immediate care of the patient and yet unsafe to engage in less patient related performance conversations despite the presence of multiple positive interpersonal factors. The concept of a safe ‘container’ (contained space) is perhaps idealised when it comes to feedback conversations about performance in the informal and emergent spaces of postgraduate training. More research is needed into understanding how clinical environments can sanction feedback conversations in clinical environments.