Anonymity is fundamental to digital privacy, but the means of ensuring it are limited. The classic view of anonymity was to make individuals indistinguishable within an anonymity set, but more recent analyses show that it is vulnerable to attacks based on background knowledge. At the societal level, tools such as TOR, which offer a degree of protection to journalists etc. are appreciated, while at the same time being stigmatized because of their connection to the darknet. Accountability is demanded here, which is diametrically opposed to anonymity. In parallel, arguments such as “nothing to hide” in liberal democracies portray transparency as freedom and anonymity as guilt. This suggests that anonymity is not needed at all. These competing perspectives reveal the paradoxical role of anonymity: it is both indispensable for democracy but often controversial in social, political and cultural discourses. In this paper, we examine precisely this conflict and offer a solution that attempts to incorporate different perspectives.