All drivers have to be prepared for driving with changed conditions, either intrinsic or external to the vehicle. This study explores factors influencing the cautiousness while driving of high school students in a rural and small semirural town community in New South Wales. Perceptions of caution in response to a range of different conditions including driving with passengers, bad weather, driving an unfamiliar car, poor road conditions, driving in heavy traffic and darkness - all conditions which have the potential to affect driving style or speed - were reported. Many of the young rural students reported having started to drive at a very young age (often off-road). This reduced their reported perceptions of caution in their later driving, on-road, post-licence. Previous involvement in a crash was linked with a less cautious approach to changed lighting conditions when driving. Targeted road safety campaigns for young rural drivers may be needed which focus upon promoting specific rural road hazard perception and awareness of the implications of speed and changed road conditions on driving style and cautiousness.