Remand remains a particularly punitive and painful form of incarceration for prisoners, as well as their loved ones on the outside attempting to provide support. Drawing on in-depth qualitative data collected from 61 loved ones’ supporting remanded prisoners in England and Wales, this article examines how the ambiguity and unknowns associated with this form of incarceration is particularly painful. Through the unique application of Boss’s theory of Ambiguous Loss, this article contributes new knowledge about the nature, scope and resilience shown by loved ones supporting remanded prisoners, indicating where future research and policy should be focused.