Digital-audio performance walks can be powerful performances, responding to troubling pasts, giving voice to testimony, and creating an affective geography that satisfies a participant's desire to connect with the city rather than just walk through it. Yet digital-audio performance walks also raise questions about performance and voyeurism, and the disconnection of private headphone experience, alongside issues of agency, detachment and appropriation. This article addresses key issues associated with digital-audio performance walks, using two case studies of performance walks (from Israel and Ireland), that aim to communicate politically charged and painful histories, which are at once ‘now’ and ‘then’, ‘here’ and ‘there’. The article considers some of the risks in digital-audio performance walks: dark tourism, privatization and empathic quietism. Finally, the article assesses what creative strategies are available to creators – and audiences – to make collaborative performance walks that galvanize spectators to become active witnesses.