Pondering death and the (im)possibility of a life-after-death is as old as the Epic of Gilgamesh. It is also part of the awkward encounters between hospice caregivers and the recipients of their care. Some of the unsettled beliefs and dark emotions, however, become glossed over as irrelevant to the clinical contexts. Moreover, to the extent chaplains are largely presumed to be Christian, offering solace and compassion from a particular and often proselytizing point of view, those coping with terminal illness may find their feelings inhibited or, in some cases, streamlined or censored. Hospice Chaplain, Interrupted enters this fray by acknowledging that chaplains, charged with care for patients at the end-of-life (as well as their grieving survivors), are never unbiased observers; philosophy and poetry therefore are proffered as those surprising fissures in the topography from which a healthy self-awareness and more permeable boundaries may arise. Is death itself the most consequential interruption known to the self-conscious human being? Are beliefs about life-after-death often naive and treated as trite or as ornamental to what's really happening beneath the surface? If so, might the spiritual caregiver offer a unique service to believers and non-believers alike by interrupting their seemingly comfortable certainties? Not all interruptions are rude, uncouth, or insensitive; some hold space for thoughts that cannot ultimately be thought and for feelings that seem too unfaithful to express.