Urban transportation systems tend to operate most effectively when common expectations exist about all user travel behavior under various conditions. A wide range of behavior among cyclists presents a significant challenge to the achievement of safer and improved designs at intersections. In this research, cyclists were observed (i.e., through the use of video at fixed-camera locations) as they made left turns at six intersections in Toronto, Ontario, Canada. The intersections were classified into five types on the basis of their physical designs and operational characteristics. Cyclist behavior was assessed to determine the propensity to traverse the intersection legally, designated as “rule compliance.” Further, the analysis determined the likelihood that a cyclist would traverse an intersection in a path that was consistent with the design; this outcome was defined as “facility compliance.” The results revealed that the presence of bike boxes, two-phase lefts, and turning lanes with advanced green phases positively influenced cyclists by increasing the likelihood that left turns would be legal and consistent with the behavior intended through the design. The results also suggested that the highest rates of rule and facility compliance existed under the condition in which cyclists approached an intersection during a green signal. On the basis of the observations in the research, design recommendations were made to accommodate cyclists better and produce more consistent behavior and presumably to enhance safety.