Introduction: The objective of the study was to explore the aspects of work-based learning environments and to identify the factors that stimulate or inhibit learning based on the theoretical framework of experiential learning. Utilizing Kolb’s learning cycle, the authors aimed to describe, compare and analyze two learning situations in undergraduate medical education, and to consolidate recommendations based on the theoretical principles. Methods: Data collection was done through a qualitative approach by interviews and observations at two institutes for 4th year undergraduate medical students in a tertiary hospital in Malaysia and in Singapore. Results: Kolb’s learning cycle stages can be linked to the learning situations. Both institutions had the problem of high student to educator ratios. There was limited opportunity for the students to examine and present patients. Time limitation was another constraint as not all students could perform physical examinations. These inadequate opportunities to apply knowledge and active participation limited the “concrete experience”. As discussion and feedback sessions were insufficient, the “reflective observation” and “conceptualization” stages were also compromised. Educators had difficulty determining if students made sense of the cases and if their learning was adequate. “Active experimentation” was also limited to end-of-posting examination only. Conclusion: Kolb’s learning cycle from the experiential learning theory can be used in these learning contexts to identify methods to improve students’ knowledge and skills acquisition, as well as to encourage reflection and applied learning.