Tasks in complex, dynamic environments typically require many activities, including information seeking, communicating, coordinating, judging, decision making, and implementing decisions. In this paper, we examine how humans choose and organize these activities using a range of contextual control modes (CCMs) as described by Hollnagel: strategic, tactical, opportunistic, and scrambled. These CCMs ... [Show full abstract] are viewed as responses to contextual features, such as time limits and task demand. We specifically examine contextual control modes during an airline schedule adherence task and evaluate potential measures of these tasks in a controlled experiment using student participants. In the first portion of the experiment, we varied the time limits and in the second, we introduced a sudden increase in task demand. Information-seeking behaviors and participant solutions were recorded. NASA TLX workload ratings and participant self-assessments of contextual control mode were assessed. Participants reported operating in and transitioning between different contextual control modes in response to time limits and task changes. CCMs did not correlate with TLX ratings of demand and effort but did correlate with TLX-frustration and TLX-performance ratings and with time limits. The results suggest that high performance may be achieved in different contextual control modes and that the design of support systems should aim to support multiple modes.