The point of departure of this paper is the striking similarities between the dispositions critical media literacy education aims to cultivate and the characteristics conspiracy theorists claim to embody. The golden question of critical literacy, “who benefits?” is in fact the central question of conspiracy theorists: “cui bono?” While critical media literacy educators teach learners to disrupt the common sense, to interrogate multiple viewpoints, to focus on sociopolitical issues, and to take actions and promote social justice, conspiracy theorists claim that (...) they do exactly those things. What I wish to illuminate through this juxtaposition, however, is not a way to clearly demarcate “critical” from “conspiratorial” theorizing, but is a question of educational desirability of skepticism. Skepticism in this paper is not understood as a classical epistemological question of the possibility of knowledge attainment, but as a form of vigilance toward epistemic authorities like the government, media, and academic institutions. Drawing on philosophy of conspiracy theories and political epistemology, I illuminate the problem of radical skepticism that characterizes some conspiracy theories and discuss the pivotal epistemic role of trust. Through this, I claim that critical media literacy education for democratic citizenship must strike a balance between cultivation of skepticism and building of trust toward epistemic authorities. (shrink)