At a time of considerable organisational change within Probation Services, the authors describe a new initiative to offer psychoanalytically-informed clinical supervision to frontline probation officers, linked to the development of a care pathway for offenders with personality disorders. An analysis of feedback forms from supervisors during the first months of this project highlighted the typical countertransference challenges of probation work. In subsequent months, concerns about organisational change were increasingly evident in supervision, possibly amplifying existing concerns about risk, formulation and management of countertransference responses. The complexities of offering containment and supervision to probation officers, at a time when they were anxious about the security of their organisational ‘container’, are explored.