Observational studies are common in the field of environment-behavior and they investigate the causal effects of environmental design on people through action-reaction behavior. The quality and strength of evidence provided by an observational study is determined largely by its design and how it is conducted. This paper employed observational study to learn about the usability and challenges encountered in the use of a commuting system in Mumbai, India. The study determined the influence of the physical environment on diverse users to outline environment-behavior issues and the level of environmental misfit that exists between users and the railway stations and local trains. The study concludes with design questions for further investigation through experimental research and interviews. Why do people avoid using stairs and instead choose to cross railway tracks? How does the two way traffic flow impact navigation on the station while commuters board or alight trains? What factors contribute to people collision on stations?