The construction contract conditions shall ideally be drafted in such a manner that provides for a balanced allocation of risks between the parties to any such contract. The project management teams, inclusive of contract administration professionals forming part of such teams, are then faced with decisions that are to be made on day-to-day basis in respect of observing the called-for contractual requirements. Those decisions pertaining to the initiation of claims and contributing to their progression are of the most difficult to administer and put in place, owing to such actions being at times viewed as detrimental to the relationship between the parties, both at the project operational as well as the corporate levels. This paper discusses the factors that come into play when such critical decisions get to be evaluated. As such, it presents a holistic perspective of the kinds of pressure expected to be prevailing over the involved decision-making process. The argued considerations are informed by a number of practical dispute resolution cases and the scenarios that have emanated under them. The paper concludes by providing guidelines that can help draw the line between the necessity of acting in fulfillment of the concerned contract callings and the process of preserving the relationship between the parties to the contract.