In less than a decade, with the emergence of food delivery platforms, cycling has gained increased visibility on city roads across the world. For the first time since the advent of the automobile age, the bicycle is re-emerging globally as a dependable tool to earn a living. Food delivery start-ups such as Deliveroo, Uber Eats or Glovo enroll an increasingly precarious population as self-employed contractors to whom they grant little social protection. Having access to a bicycle and knowing how to use it is a very low entrance requirement for these jobs. Cycle food couriers hold a precarious entitlement to the road space, which makes them constantly vulnerable to bodily harm, and is compounded by a broader ontological precarity. The insecurity resulting from being engaged in an unregulated gig economy where job and income instability is amplified by issues of gender, ethnicity and migration status, further adds to road unsafety. In this chapter, we draw on case studies from the UK, Spain and South America to account for how the precarity of cycling is amplified by the political landscape of neoliberalism of the last three decades, which promotes flexible work, and the legislative setting failing to account for cycle couriers as employees.