The ancient and sacred task of timekeeping, linking the eternal with the everyday, is one of the oldest missions of astronomy, originating long before the dawn of written history. The succession of timekeeping schemes throughout millennia has been a search for a balance between the practical and the symbolic. In the current Leap Second Debate, there are rational arguments, focused on practical considerations, and there is a certain unspoken unease, emerging from the symbolic substrata of the issues involved.Developing our work presented at the Exton and Charlottesville colloquia, this paper will examine the presuppositions and perceptions overshadowing the debate: astronomical conformity, continuity, timelessness, (ir)rationality, the Enlightenment, etc. We shall study the historical evidence represented by the various calendric traditions and situate the Leap Second Debate in a broader context of cultural history and history of thought. Our underlying purpose is to facilitate the debate by shedding some light on its caliginous but potent undercurrents.