Claims and disputes are considered an inevitable consequence of the construction process, and project participants are becoming more aware of their costly and lengthy resolution process. The conditions of contract normally include procedures for the submittal, administration and resolution of claims, while it is widely recognized that attempting to resolve claims/disputes through amicable settlement as opposed to arbitration or litigation can save on a lot of time and money. This paper presents a critical analysis of the windows of opportunities offered under both the 1987 and 1999 FIDIC conditions of contract for attempting to resolve claims/disputes amicably. It first focuses on the 56-day period specifically dedicated for attempting an amicable resolution of disputes and highlights the possibilities of effectively stretching this period in more than one way. It further explores the opportunities available at the earlier stages of the claim/dispute timeline, before a claim is escalated to the level of a dispute.