This paper contributes to filling a lacuna in our knowledge of penal history in Scotland by examining the voices of convicts through records of prisoners experiencing Penal Servitude during the period 1897-1942. The sources utilized are the archived files of thirty-two male convict prisoners in Scotland’s Convict Prison at Peterhead. These files give insights about life in this remote prison as conveyed through records of punishment, prisoners’ requests, and prisoners’ letters. Prison Rules about convict correspondence highlight penal letters as a distinctive genre of communication: political and personal boundaries were enforced on all exchanges. The convict prison, like nineteenth-century British labour colonies, imposed workhouse conditions at the extreme; it was a place of exclusion, dominated by religious and social sentiment and suppositions about criminal psychology and containment. The extent of the curtailment of convicts’ liberty and the aim of re-socialization is refracted in penal practices fostering convict dependency. The ethos of Scotland’s convict colony was immersed in military traditions of training, subservience to authority and generalized gloom.