Deceptive communications strategies are further problematized in digital space. Because digitally mediated communication easily accommodates pseudonymous and anonymous speech, digital ethos depends upon finding the proper balance between the ability to create pseudonymous and anonymous online presences and the public need for transparency in public speech. Analyzing such content requires analyzing media forms and the honesty of speakers themselves. This chapter applies Michel Foucault’s articulation of parrhesia—the ability to speak freely and the concomitant public duties it requires of speakers—to digital communication. It first theorizes digital parrhesia, then outlines a techno-semiotic methodological approach with which researchers—and the public—can consider online advocacy speech. The chapter then analyzes one case of astroturfing, and one of sockpuppteting, using this techno-semiotic method to indicate the generalizability of the theory of digital parrhesia, and the utility of the techno- semiotic approach.