This paper examines the intersection between the career of a Sufi Shaykh and the media. It focuses on Indonesia’s most influential contemporary Sufi scholar of Hadrami-descent, Habib Luthfi bin Yahya (b. 1947), particularly on his engagement with different media forms over the course of his career. Habib Luthfi began as a Sufi Shaykh and a mobile preacher who provide religious guidance to rural Javanese communities. Many of his audience has joined his tariqa(Sufi order/brotherhood) to become formal disciples. In 2003, a newly established bimonthly Islamic magazine, AlKisah, introduced a Q&A rubric dedicated to Sufism and requested Habib Luthfi to become its expert host. Having his own rubric allowed Habib Luthfi to become known as an authority of Sufism outside of his traditional ṭarīqacircle. His answers to various questions relating to Sufism has been collected into a widely-circulated book that has been reprinted multiple times. With the increasing popularity of social media, however, the market for Islamic magazine dwindled, and AlKisahclosed down. In 2010, however, several of Habib Luthfi’s disciples established the official website, facebook page, and twitter account of their spiritual master with the aim to spread his ideas. By presenting a short history of Habib Luthfi's engagement with different media forms, this paper observes and compares the contrastive relationship of authority formed in and through different media engagement. Rather than treating media simply as channels of communication and dissemination, the paper interrogates how distinct forms of mediatization qualitatively transform a relationship of authority in contrasting ways, generating excitement on the one hand, but also anxiety.