The current emphasis on organizational transparency signifies a growing demand for insight, clarity, accountability, and participation. Holding the promise of improved access to valid and trustworthy knowledge about organizations, the transparency pursuit has great potential for enhanced organizational effectiveness and widened democratic practice. Yet, with its most common operationalization, as information, transparency reinstalls a 'purified' notion of communication devoid of mystery, inaccuracy, and (mis)representation. We apply transparency to itself by unpacking its implicit model of communication and critiquing its obliviousness to the representative nature of transparency-related messages and the attendant complexities of motivation. This critique interrogates the ambiguities and ambivalence of the transparency pursuit and demonstrates how the goals of organizational transparency are counteracted by new types of opacity.