Background: Tracheal intubation is an essential skill for anaesthetists and other disciplines that require emergency establishment of a secure airway. Early attempts in patients often meet with failure. Existing publications focus mainly on trainees in emergency settings and highlight the role of experience in success; most recommend prior simulation training. Common factors identified as contributing to difficulty have been difficult airways, emergencies and rapid sequence induction. Early intubation skill development in patients with anticipated straightforward airways in a controlled environment has received little attention. Objectives: This qualitative observational study aimed to identify common difficulties associated with a supervised intubation process by inexperienced personnel in the relatively stress-free conditions of elective surgical procedures in the operating theatre. Methods: Following institutional and ethical approval, participants, supervisors, anaesthetic assistants and patients consented to observation and video-recording of supervised intubations in a Durban teaching hospital. Anonymity and confidentiality were assured. Contemporaneous observations were recorded in theatre, and video-recordings were subsequently reviewed for content. Errors, and interactions between supervisor, assistant and participant, and associated outcomes, were identified. Results: Twenty participants (medical interns and medical, paramedical and nursing students) performing 72 intubations were observed. All participants had prior training using manikins or simulators. There were 61 successful intubations and 11 unsuccessful attempts. Factors associated with failure included unfamiliarity with airway, equipment or process. Process errors included inadequate head positioning, laryngoscope handling and tracheal tube manipulation. Anaesthetic assistants contributed to difficulties in some cases. Supervisor support was either verbal, physical or both. Less experienced supervisors tended to intervene earlier. There was a significant trend for success associated with the reported number of prior successful intubations. A successful intubation within the study was, however, no guarantee of subsequent success. Conclusion: Despite prior simulation training, many participants demonstrated lack of familiarity with the airway, intubation process and equipment. While improved simulation training might partly address these issues, supervision of early clinical intubation attempts needs to be redirected from the process of intubation itself to the process of intubation skills acquisition. A first step would be to ensure that all supervisors and assistants are trained for the latter goal, anticipating common errors and providing standardised conditions for success. The use of video-recording of the events is an invaluable aid to observation and interpretation, and is recommended as an adjunct to further studies of mechanical skills transfer.