This chapter questions the common understanding that lack of trust is negative to strengthening democracy and that public lack of trust signals that a liberal democracy is in crisis. It notes how the contemporary drift toward authoritarianism within many established liberal democracies is often coupled with the ideologization of surveillance policies and practices to echo the discourses and goals of far-left and far-right populism. It then clarifies how a democratic lack of trust within civil society can constructively stem these drifts toward authoritarian tendencies, which are so commonly enabled by state and corporate surveillance practices. In order to do so, it establishes notions of trust, trustworthiness, and intelligent accountability and develops a militantly democratic approach to oversight of surveillance by civil society. Subsequently, three country-based cases are explored: Germany, Poland, and the United States, which share the political encroachment of far-right populism to varying degrees. Critically analyzing these cases clarifies the importance of a militant democratic approach to curtailing authoritarianism and also to reimagining and resemantizing the power and knowledge dynamics existent between civil society, the state, and corporations, in order to enable democratic oversight and ensure security upholding human rights and civil liberties.