After a number of cyclist deaths over recent years in New Zealand, cycle advocates and policy makers have been pondering the issues relating to safety of cyclists on New Zealand roads. Press reports have highlighted a number of recent cyclist deaths and the subsequent public dismay as to how guilty motorists often walk off with a lenient sentence. There is strong public feeling that, in the absence of an appropriate penalty system, the roads are not safe to cyclists. The present New Zealand law provides for specific offences and related penalties when the driver, who drives carelessly or dangerously, kills or injures another road user. This thesis investigates whether the law as understood through both the legislative regime and the interpretation of the law by the courts, is sending the right deterrent message against careless or dangerous driving, hence making the roads safer to the cyclist. This is explored through an analysis of the legislative provisions on road safety and their interpretation by the courts in cases of collisions by the careless or dangerous driver and an assessment of the severity of the penalties and consistency of the penalties imposed in similar cases. The study draws on existing literature which indicates that safety, real and perceived, or rather a lack of safety, remains a significant barrier to cycling. It then explores the extent to which road safety is made a top priority on the agenda of different stakeholders, particularly, policy makers, legislators and judges. The study also draws a comparison with the policy and legislative regime in more cycle friendly countries like the Netherlands. The severity of the penalties imposed on the careless or dangerous driver in England is also addressed. This study concludes that the promotion of road safety is key to a modal shift in New Zealand. To allow this, it is not merely the right policies that are called for, but also for all stakeholders to have a shared contribution. The study comes up with a number of recommendations that would help pave the way towards law reform with a view to promoting cyclist safety on New Zealand roads.