This essay explores how particular variants of “Muslim anarchism”, as distinct forms of radical anti-authoritarian religion, subvert conventional approaches to Islamic hermeneutics by drawing on intellectual traditions and discursive strategies external to them. Through recourse to the mutuality between autonomy and automatism, most notably in Western avant-garde and countercultural aesthetics, it elucidates the import of automatic transcendence and retro-futurist imaginaries as novel interpretative techniques for spiritual emancipation in radically libertarian approaches to Islam. My aim is to show how the rich, multivalent concept of automatism, neglected in studies of social and religious phenomena, can be a useful way of elucidating the hermeneutics of specific strands of Muslim anarchism. In doing so, the paper also challenges received understandings of “radical” Islam and the restrictive polarity between militancy and liberalism that has come to frame discussion on global Islam. To this end, I focus on the thought of Peter Lamborn Wilson (aka Hakim Bey), Michael Muhammad Knight and Yakoub Islam.