Dexter Daniels' role in the Wave Hill walk-off has cemented his place in Australian history. This paper, however, examines a lesser-known though related incident: Daniels' arrest for vagrancy in December 1967. His arrest is curious. He had money in his pocket and was actively seeking work. It was his reputation for political and industrial agitation, rather than wilful indigence, that lay at the heart of his arrest. His conviction draws attention both to the political intent of vagrancy laws and the inequity of their application. Such laws, many of which have now been repealed and their provisions diffused elsewhere in the criminal code, were used extensively in Australia. With their 'moral' underpinnings and lax evidentiary requirements, they became convenient mechanisms to isolate and punish 'anti-social' behaviour. Drawing on files held in the National Archives, this paper attempts to explain why Daniels was targeted in this way and why a seemingly insignificant conviction made headlines in the southern states' metropolitan newspapers and captured the attention of the Prime Minister and Cabinet as well as the resources of several government departments.