Drawing on archival research and oral history interviews, this article compares the characteristics of the relationships between police officers and communities in the Glasgow conurbation with those in the highlands and islands of Scotland in the period c. 1900–70. Rejecting the uniform or linear narrative suggested by existing historiography, it argues that these relationships were diverse, complex and shaped by local cultural, social and economic factors. By analysing the grassroots or everyday policing delivered by the urban beat officer and village constable, it reconstructs a social history of policing in twentieth-century Scotland. Moreover, the article identifies key constitutive elements that enabled or disrupted the forging of trust and legitimacy in Glasgow and the highlands in an era still associated by some with a ‘golden age of policing’. The article focuses in particular on the capacity of discretion, ‘insider’ status and embeddedness within local settlements to deliver effective policing, enhancing conclusions about best practice that have been drawn from studies of more recently formalized ‘community policing’ initiatives.