Urban exploration is a practice of researching, rediscovering and physically exploring temporary, obsolete, abandoned, derelict and infrastructural areas within built environments without permission to do so. Drawing from four years of ethnographic research with a group of urban explorers in the United Kingdom who undertook increasingly brazen forays into off‐limits architecture, this paper argues that while urban exploration can be connected to earlier forms of critical spatial engagement, the movement also speaks to the current political moment in unique ways. Urban explorers are one of many groups reacting to increased surveillance and control over urban space, playfully probing boundaries and weaknesses in urban security in a search for bizarre, beautiful and unregulated areas where they can build personal relationships to places. The results of this research both complement and complicate recent work within geography around issues of surveillance, subversion, urban community building and critical engagement with cities.