Hospital chaplains perform important activities, but critical questions arise about the challenges they may face in working with patients, and how these professionals respond. Thirty-three telephone interviews of approximately 1 hour and were conducted with 21 board-certified chaplains. When asked about their biggest challenges and most rewarding interactions, several chaplains described rejections by patients or families. Patients and families at times rejected chaplains, and did so for six broad types of reasons – not wanting to discuss the disease due to conflicted feelings, including anger or frustration at the patient, the cosmos or God; or wanting to minimize it; wanting a chaplain of their own faith; or of a particular gender or other characteristic; being atheist or wary of religion; or misunderstanding what chaplains do. Patients at times also disagreed with family members about whether to reject a chaplain. Chaplains responded variously: feeling transitory hurt (which generally decreases with experience); respecting patients’ autonomy and leaving; exploring reasons for rejection; and revisiting later and often then making helpful connections. These data have important implications for future practice, education and research regarding chaplains and other providers – suggesting, for example, how patients’ families and the public might benefit from increased understanding about the field.