With the increasing adoption of driving automation technologies, vehicles equipped with SAE Level 3 driving automation are becoming available on the market. This study explores drivers’ behaviour when driving conditionally automated vehicles on-road, providing multiple levels of driving automation. Sixteen participants drove a Wizard-of-Oz vehicle offering several levels of automation (Manual, SAE Level 2 and Level 3) on a public highway. Data was collected during driving sessions (observations and think-aloud) and post-driving sessions (in-depth interviews). The results indicate that drivers show errors in mode transitions and mode awareness. These errors include unintended deactivation of Level 2 driving automation, confusion about driving modes after disengaging Level 3 driving automation, and confusion about the current driving mode. These findings highlight a fundamental limitation in the design of automation systems when humans are required to operate multiple modes within a single system, making it challenging to distinguish between them clearly. This ambiguity and lack of understanding affected how drivers interacted with, interpreted, and responded to the automated vehicle. The study provides insights for designing automated vehicles with multiple levels of driving automation, aiming to improve mode awareness and overall safety.