Although most diplomatic tasks resemble day-to-day bureaucratic routines, it is during crisis and conflict management that diplomacy manifests its value-added as well as its limits. Under such exceptional circumstances, messy in terms of order and fuzzy in terms of power, diplomats are expected to strike a path out of impasse. This paper examines the diplomatic mediation efforts in three intractable conflicts, which failed to deliver an acceptable settlement. Most analyses account for failure of peace talks with recourse to fixed interests and incompatible goals of the involved actors. In contrast to such approaches, this paper examines whether and how mediation processes themselves rigidified the deadlock or even exacerbated the conflict. More specifically, this paper takes a closer look at “soft” factors such as fairness and recognition, which often elude the theoretical nets of foreign policy analysis, in order to account for the derailment of diplomatic efforts. This study distinguishes thereby three dimensions: First, the ambiguous normative context of mediation. Mediators and conflict parties are subject to two often competing paradigms, the one of state-building –prioritizing security–, and the one of peace-building –prioritizing sustainable settlement of the conflict. Second, the mediators´ stronger focus upon either the outcome or the procedure of conflict resolution. Diplomats are often confronted with the dilemmas of law-conform procedures which may nevertheless produce illegitimate outcomes, as well as of legally contestable procedures which may still produce mutually acceptable outcomes. Third, the contentious issue of engaging key state, non-state, and sub-state actors besides the conflict parties into the conflict resolution process. Mediators often fail to avert or contain spoiling behaviour by such third actors by giving them too little, or too much leverage at the wrong moment in the process. The paper attempts to elucidate the interplay between foreign policy preferences and non-intended consequences of diplomacy along three illustrative cases, those of Cyprus, Nagorny-Karabakh, and Kosovo, mediated by the UNO or the OSCE during the past decade. Furthermore, it raises the question whether conforming to the established rules of the game under such extra-normal conditions is more productive than modifying, or breaking them, and introducing new ones.