This thesis investigates how men who have sex with men (MSM) discern, discuss, and defy issues of surveillance in the context of casual, public sex—also known as cruising—and how these exchanges constitute and inform subaltern countersurveillance measures. Focusing on written exchanges by users of the queer hook-up website Squirt, I analyze how users discuss safety and surveillance of cruising locations in the Greater Ottawa Area. This work concludes that surveillance and cruising is normalized, both police and ordinary citizens present safety risks, great care is taken to act discreetly and not infringe on the safety of non-cruisers, and environmental factors contribute greatly to the construction and circumvention of surveillance infrastructure. The data additionally complicate well-established perspectives on surveillance, including surveillance realism and introduce opportunities for queering and expanding future research.