Wearable computing technology is increasingly being used to monitor people anywhere and anytime. Today, automated biometric identification, radio-frequency identification (RFID) tags, and global positioning system bracelets have all changed the way that people are being tracked and monitored within corrective services. Prison inmates, for instance, entering prisons that are RFID-enabled and wi-fi compatible, are fitted with RFID bracelets upon entering a facility, enabling guards to track their location 24x7 at two second intervals, if required. Low-risk offenders serving their sentences from home or persons on parole can also be fitted with similar devices which can track their outdoor location down to 10 metres of accuracy on average using positioning satellites. This paper speculates on the question of whether permanent monitoring (at least for the lifetime of ones prison sentence or parole period), works against rehabilitation by drawing on primary data gathered from free persons tracked 24x7 during a field trial.