Open Government is en vogue, yet vague: while practitioners, policy-makers, and others praise its virtues, little is known about how Open Government relates to bureaucratic organization. This paper presents insights from a qualitative investigation into the City of Vienna, Austria. It demonstrates how the encounter between the city administration and “the open” juxtaposes the decentralizing principles of the crowd, such as transparency, participation, and distributed cognition, with the centralizing principles of bureaucracy, such as secrecy, expert knowledge, written files, and rules. The paper explores how this theoretical conundrum is played out and how senior city managers perceive Open Government in relation to the bureaucratic nature of their administration. The purpose of this paper is twofold: first, to empirically trace the complexities of the encounter between bureaucracy and Open Government; and second, to critically theorize the ongoing rationalization of public administration in spite of constant challenges to its bureaucratic principles. In so doing, the paper advances our understanding of modern bureaucratic organizations under the condition of increased openness, transparency, and interaction with their environments.