The COVID-19 pandemic has been, and still is, a worldwide health crisis. Despite the surge of literature on this phenomenon, little research has been conducted with the Probation Service during this time. The aim of this research was to explore Probation Practitioners’ (PPs’) experiences of the COVID-19 restrictions with a specific focus on those who access the Psychologically Informed Consultation Service (PICS). Further, to explore the experiences of key aspects of the COVID-19 pandemic through the lens of the Community Offender Personality Disorder Service. Semi-structured interviews were conducted with 9 PPs who represented a broad cross-section in terms of age and years of experience in the role. Interpretative Phenomenological Analysis was used to explore the experiences of PPs and revealed 5 main themes: unmet support needs, problematic working environments, an emotionally distressing time, the use of PICS, and a silver lining. These findings are discussed with implications for further research.