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This paper analyzes the historic move to modify the role of secrecy towards third parties in diplomatic negotiations, and its political significance. An undisputed norm during the Renaissance, secrecy could veil both the negotiation process and its outcome. This was then contested from the Enlightenment to Wilson’s ambition for open diplomacy. In contemporary times, an order of transparency is gradually exposing negotiation arenas and processes. From this perspective, this paper examines the justifications and risks of secrecy and transparency toward third-parties. As neither can permanently exclude the other in the negotiator’s strategy, we show that the issue of secrecy and transparency constitutes a dilemma between efficiency of the process and legitimacy of the outcome.