Recent techniques for indoor localization are now able to support practical, accurate turn-by-turn navigation for people with visual impairments (PVI). Understanding user behavior as it relates to situational contexts can be used to improve the ability of the interface to adapt to problematic scenarios, and consequently reduce navigation errors. This work performs a fine-grained analysis of user behavior during indoor assisted navigation, outlining different scenarios where user behavior (either with a white-cane or a guide-dog) is likely to cause navigation errors. The scenarios include certain instructions (e.g., slight turns, approaching turns), cases of error recovery, and the surrounding environment (e.g., open spaces and landMarks). We discuss the findings and lessons learned from a real-world user study to guide future directions for the development of assistive navigation interfaces that consider the users? behavior and coping mechanisms.