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The landscape of the Probation Service in England and Wales continues to be challenged by issues of priorities, workload, and lack of meaningful relationships between offenders and practitioners. In this climate of uncertainty and ‘transformation’, vulnerable offenders on probation become the ones mostly affected due to management plans and license conditions that do not respond to the variability of their needs. This chapter explores the older individuals on probation and uses the framework of Multi-Agency Public Protection Arrangements (MAPPA) to examine the extent to which it may accommodate the needs of this group of offenders in an otherwise risk-based context. This study draws ideas from previous research of the author and aims to develop the existing limited academic attention that older offenders supervised under specialised probation contexts have received. The structure of the chapter remains doctrinal in nature as a response to the need for a more comprehensive and inclusive perception of the risk of reoffending later in life and its implications for bespoke community reintegration strategies. This approach also allows for theorisation of MAPPA’s multi-agency structure and its prospects for the rehabilitation of older offenders. This study finds that as MAPPA only manages violent and sexual offenders, the ‘older MAPPA offender’ becomes a special category for probation that may exhibit a variety of needs and life circumstances. It thereby becomes even more important for these offenders that a constructive working relationship between them and the probation officer is in place. This supports the latter in appreciating what factors lead the individual to offending later in life, and what interventions may be most effective to address their risk of reoffending as well as their needs in the community.