Since the start of the COVID-19 pandemic, online supervision has increased markedly, including within the Dutch probation services. In the present research, we systematically collected and analysed both clients and probation officers’ experiences of working online in the prior year. Although the clients were generally positive about remote supervision, some expressed that they missed the personal contact. According to most of the probation officers, remote working is flexible (efficient, saves time, travel costs), appropriate for certain phases of the probation process (especially at a later stage when a working alliance has been established) and particularly suitable for probationers with mild problems and low risk profiles. The general experience was that conversations are both more pragmatic and business-like, which, in turn, can produce both strengths and limitations. Once a foundation has been established, it appears to be possible to continue working remotely with clients, albeit the probation officers stressed that this depended on the type of client, type of offence and risk level.