Given that decision makers continue to face dilemmas on whether to persist or desist with troubled projects, it is important for senior managers to support the assessment of decision dilemmas faced by project managers. By drawing on two case studies that exhibit project escalation situation, decision-makers in both cases were interviewed and important documents reviewed, the paper has identified five types of decision dilemmas and their associated characteristics: justification, sunk cost, ambiguity, opportunity cost and completion. The decision dilemmas identified in this study and the recommendations for countering these dilemmas aim to help project managers improve the process of decision-making during project development. Furthermore, it is also important for organizations to be aware of the role played by decision dilemmas within the escalation phenomenon as such understanding could help organizations extricate themselves from future escalation predicaments.