This paper presents the findings of a semi-structured interview study that was conducted to identify drivers' self-reported likelihood of engaging with technologies that are now commonly found in modern automobiles. Previous research has focused on the effect these technological tasks have on driving performance, but there has been less focus on how, why and when drivers choose to engage with them. As distraction remains a significant contributor to road accidents, an understanding of why it occurs will give important insights into how it can be prevented. A semi-structured interview schedule was developed to allow drivers to discuss the factors that influence their decision to engage with a variety of different technologies. The methodology facilitated both quantitative ratings of the drivers' likelihood of engaging in a variety of tasks and qualitative insights into why. Age and gender had some influence on the propensity to engage, in line with other findings in the literature, as did road type and task type. The reasons drivers gave for why they engage with potentially distracting tasks inform recommendations for preventing distraction related accidents from the increasingly prevalent sources of technologies available to drivers.