Given that only a small proportion of mentally disordered offenders will receive disposals under the Mental Health Act 1983 it is highly likely that a significant proportion of individuals with mental health problems will come into contact with probation services. This can either be through the imposition of a community order or following their release from custody on licence if they have served a determinate, extended or life sentence. Probation officers, therefore, have a significant role in the supervision of offenders with mental health problems in terms of helping them access services and alleviate personal and practical difficulties that might increase their vulnerability. Moreover, as Robinson contends, exposure to the criminal justice system in itself can induce feelings of social isolation and stigma that might lead to a deterioration in an individual’s mental state. In the absence of other mental health professionals, it often falls on probation staff to recognise mental health issues and to make appropriate recommendations to the court through the provision of a Pre-Sentence Report. For this reason, the Bradley Report (2009) recommended that all probation staff should receive mental health awareness training, having found that existing provision was often non-existent or wholly inappropriate. This chapter presents challenges and controversies in this field, with an invitation to the reader to consider policy and practical issues in the context of those offenders with mental vulnerabilities.