An escalation of environmental concerns, rising petrol prices, and increasing health concerns has led to a re-emergence of cycling as a viable transport alternative. The impact of this resurgence led to friction in communities that have a less established cycling culture. Lightweight point-of-view (POV) cameras that are helmet or bicycle-mounted are now becoming the “documenters” of these moments of friction, providing an impartial view of the circumstances where cyclists are negatively interacting with other road users. This paper will discuss the use of digital technology in contemporary cycling, focusing on the effects of small, lightweight POV cameras used by cycle commuters. Recent technological advances resulting in smaller and more affordable video cameras means that it is now very simple to share the cyclist’s point of view. This provides a unique simulation of the cycling experience, allowing for some insight into the phenomenology of travelling by bicycle. The addition of the ability to share these experiences online heralds a new chapter in cycling history: how has the use of digital media, both hardware and networks, affected the cyclists’ experience? Prior to the adoption of POV cameras, negative driver/cyclist incidents were so prevalent that the SMIDSY acronym was coined: “Sorry Mate, I didn’t See You”. This paper will examine the transition in circumstances that fostered the increased need for cycle commuters to adopt cameras as a defensive mechanism by discussing three parallel developments: the re-establishment of cycling as transportation, the progress in camera technology, and the online networks that support the sharing of experiences. This paper will then consider how these factors combined to encourage the increased use of POV cameras and the extended social effects on the relationships between drivers, cyclists, and pedestrians on the road. The consequences of these driver/cyclist collisions undoubtedly put the cyclist at a severe disadvantage. As these devices become more affordable, we are seeing them used in wider contexts. The most popular utility of these cameras are for commuters to share videos of other road users’ errors. The social effects of ubiquitous media devices that capture and share our cycling experiences are divisive; these shared videos are provocative and garner very strong opinions on all sides. These shifting patterns—evolving road user composition, the corresponding shift in driver and cyclist mentalities, and the emergence of affordable digital media devices—mark a wider period of change in the social behavior of road users.