This study investigates Avalokiteśvara’s psychopomp function by tracing how the bodhisattva’s identity as a guide of souls surfaced and reemerged in select ritual-visual contexts from ninth-century Dunhuang to twentieth-century Chosŏn Korea. Taking Aurel Stein’s early attribution of a Dunhuang votive painting—now known as the “Guiding Bodhisattva”—to Avalokiteśvara as a point of departure, it explores how localized esoteric practices and artistic innovation forged new iconographic and soteriological possibilities. Close readings of Guiyijun-period woodblock prints and votive paintings show that Avalokiteśvara’s guise as Yinlu pusa, “the bodhisattva who shows the way,” developed outside canonical prescriptions, shaped by regional ritual and pictorial conventions. The guiding motif later diffused into Chosŏn Korea’s Pure Land tradition, where Avalokiteśvara reappears prominently as the “Guiding King” in dragon-boat paintings ferrying souls to paradise. The study argues that Avalokiteśvara’s psychopomp imagery constitutes a transcultural construct sustained through the circulation, adaptation, and localization of ritual and artistic practices. This continuity demonstrates how Buddhist iconography negotiates diverse religious aspirations while preserving thematic cohesion across time and space.