Strategic decision making under uncertainty has been typified as an uncertainty mitigation activity. However, this hypothesis breaks down under conditions of very high uncertainty as it demands judgment on the part of managers. Research on this topic is sparse. To decode the black box of judgment under very high uncertainty, this paper uses an unconventional qualitative technique of examining managerial judgment under four anticipation-outcome scenarios. The findings suggest that judgment in a confirmatory scenario is influenced by internal factors such as organizational capabilities. In contrast, judgment in a contradictory scenario is influenced by external factors such as strategy of competitors.