Situated learning characterises the learning that takes place in the clinical environment. Learning in the workplace is characterised by transferring classroom knowledge into performing tasks and this may take various forms. In the medical education field, the cognitive apprenticeship instructional model developed by Collins (2016) supported this learning in the workplace setting due to its common characteristics of apprenticeship. This paper analysed two concrete learning situations in a Malaysian undergraduate and an Omani postgraduate learning environment. Both learning situations occurred in the primary healthcare outpatient setting. The cognitive apprenticeship model was used to identify characteristics of the individual learning environments and discusses factors that stimulate learning. Attention was paid to the role of reflection in stimulating learning in the described settings. The paper provided the context in both institutes, described the learning situation and provided an analysis based on the theoretical framework. Based on the analysis of the situations, solutions to problems in the two settings were suggested.