This article explores the increase in the number of older people on probation caseloads. ‘Older’ clients are defined as those aged 50 and over, in line with the use of this definition by Her Majesty’s Prison and Probation Service. Drawing upon a Freedom of Information request submitted to the Ministry of Justice, the data show increases in the age of probation clients across community orders, suspended sentences, and supervision on licence. One in five residents in Approved Premises are over 50. Despite the increase, there is a dearth of research relating to the needs of older people on probation and how well probation services and staff are equipped to meet their needs. Consequently, this article utilises research relating to older prisoners, drawing inferences to probation experiences. This prompts the question of whether probation is ‘institutionally thoughtless’, a term coined relating to the daily experiences of older prisoners. This article depicts findings from qualitative interviews with older prisoners in prison for the first time. The findings highlight ambivalence towards completing accredited programmes, which may be applicable to probation settings. This article concludes that action to tackle discrimination requires a commitment to justice, self-awareness, and knowledge via policy and practice.