Parking fees and fines represent contested issues in cities, as they conflict with vehicle owners’ opinion over ‘rights’ to public space. As cities have moved to regulate vehicle density by introducing parking fees, a share of drivers may feel compelled to ‘cheat’, weighing the price of parking fees against the cost of fines, or to simply park illegally outside designated areas. To better understand these interrelationships, this paper considers negotiations of public space as an economic gamble that can be assessed on the basis of parking violations. The study is situated in Freiburg, Germany, and relies on a mixed-methods approach that investigates the views of the regulatory agency and its enforcement officers, as well as registered parking violations (n = 181,735, in 2019). Time-spatial probabilities of being fined when parking illegally are calculated as risks, defined as detection probability per “hexagon-hour”, an indicator integrating space and time. Results confirm that in the inner city, it is economically rational not to pay parking fees during 86.1% of hexagon-hours, and in surrounding areas during 99.9% of the time. Findings confirm that urban space can be negotiated in an equilibrium of fees, fines and controls. To make vehicle ownership and use less attractive, the price of parking needs to be high. Fines need to be high in relation to fees, and control densities need to constitute significant detection risks.