How do managers select media for communication and collaboration? Previous research has identified a myriad of contextual factors, individual characteristics, social factors, and the fit between medium characteristics and task requirements as influencing media choice. An implication from the cumulative research base is that managers must consider a large number of factors in the process of media selection, but task contingencies may not allow for the assessment of numerous criteria. Based on a behavioral decision-making perspective, this study proposes that task contingencies in the form of complexity, importance, and urgency influence the extent to which individuals evaluate various factors for media selection. The authors utilize data from a survey of managers in a financial organization. Under conditions of high task complexity and/or importance, managers are found to extensively appraise information for media selection. However, if the task is urgent, the extent of information evaluation during medium choice is constrained. Further, to the extent that managers’ appraisal is limited, their actual medium choice diverges from the optimal choice. The results indicate that a behavioral decision-making view can provide a fresh perspective and enhance understanding of how managers actually select media for their communication and collaboration activities.