Ibn ‘Arabi’s medieval context provided a way to think about the multiple religious roles of “sainthood” in earlier and contemporary Muslim cultures. This historical presence of the saints and in its legacy found in the developing of Islam in Indonesia particularly in Java region. Until present days, the wayang theater—first adapted as a vehicle for communicating Islamic perspectives by the formative Muslim teachers in Java (the famous “Wali Songo”)—has undergone transformations over many centuries, beginning with the moving popular representation of classical mystical texts (suluk), and evolving into an effective creative vehicle for discussing a wide range of contemporary socio-religious and ethical topics. In each of those forms, the wayang relies on the personification, figurization, and imaginative representation of spiritual guidance and communication conveyed by its familiar stories and cast of characters (lakon). Through those aspects of imagination, the viewers (and listeners) can come closer to grasping in their own lives such central dimensions of walāya/sainthood as the esoteric connections of the hidden and the manifest; the mysteries of inner spiritual knowledge (ma‘rifa or al-‘ilm al-bāṭiniyya); and the deeper meanings of life’s panoply of revealing divine “Signs” (āyāt). In each of these arenas, the manifestations of sainthood—as they are awakened and suggested by the shadow-play—provide an open-ended, ongoing vehicle of spiritual guidance, in keeping with the endless capacities of each person’s creative imagination. When viewed from the perspective of Ibn ‘Arabi’s metaphysics and epistemology, the wayang tradition itself can be understood as only one vehicle—albeit a particularly effective and persistent one—for conveying the spiritual lessons and depths of each individual’s unique religious life and encounters with the divine “closeness” and guidance (walāya) in all its transforming expressions Ultimately, the wayang shadow-theater, with its distinctive combination of characters, stories, and music, is a revealing stage for imagination to discover the deeper spiritual presence of prophecy and walāya in every domain of life. Keywords : walaya, imagination, Ibn 'Arabi, Mirror, Shadow, Society, Wayang, Plurality