Every motorised jurisdiction mandates legal driving behaviour which facilitates driver mobility and road user safety through explicit road rules that are enforced by regulatory authorities such as the Police. In road safety, traffic law enforcement has been very successfully applied to modify road user behaviour, and increasingly technology is fundamental in detecting illegal road user behaviour. Furthermore, there is also sound evidence that highly visible and/or intensive enforcement programs achieve long-term deterrent effects. To illustrate, in Australia random breath testing has considerably reduced the incidence and prevalence of driving whilst under the influence of alcohol. There is, however, evidence that many road rules continue to be broken, including speeding and using a mobile phone whilst driving, and there are many instances where drivers are not detected or sufficiently sanctioned for these transgressions. Furthermore, there is a growing body of evidence suggesting that experiences of punishment avoidance - that is, successful attempts at avoiding punishment such as drivers talking themselves out of a ticket, or changing driving routes to evade detection -are associated with and predictive of the extent of illegal driving behaviour and future illegal driving intentions. Therefore there is a need to better understand the phenomenon of punishment avoidance to enhance our traffic law enforcement procedures and therefore safety of all road users. This chapter begins with a review of the young driver road safety problem, followed by an examination of contemporary deterrence theory to enhance our understanding of both the experiences and implications of punishment avoidance in the road environment. It is noteworthy that in situations where detection and punishment remain relatively rare, such as on extensive road networks, the research evidence suggests that experiences of punishment avoidance may have a stronger influence upon risky driving behaviour than experiences of punishment. Finally, data from a case study examining the risky behaviour of young drivers will be presented, and the implications for 'getting away with it' will be discussed.