This qualitative study explored perspectives toward a good or bad death among 21 older homeless adults residing in transitional housing. Using grounded theory approach, the themes for a good death were (a) dying peacefully; (b) not suffering; (c) experiencing spiritual connection; and (d) making amends with significant others. Themes for a bad death were (a) experiencing death by accident or violence; (b) prolonging life with life supports; (c) becoming dependent while entering a dying trajectory; and (d) dying alone. Healthcare professionals need to develop approaches for end-of-life care grounded in understanding unique needs of older homeless adults.