While research has increasingly focused on the role of digitalisation in prisoners’ detention experiences, the impact of the digitalisation of the prison regime on the discretionary power of prison officers has been understudied. By using an ethnographic approach in one digital Belgian prison, qualitative interview data are used to investigate the prison officer’s coping strategies in response to the digitalisation of prison life. It is found that the gatekeeping role of prison officer’s has been partly stripped away but also that the impact of digitalisation on the prison officer’s discretionary power depends on how digital technologies are implemented. Moreover, the study reveals that not all official goals regarding the digitalisation are met and highlights the need of supporting prison officers when implementing new technologies in prison.