This paper addresses security and safety choices that involve a decision on the timing of an action. Examples of such decisions include when to check log files for intruders and when to monitor financial accounts for fraud or errors. To better understand how performance in timing-related security situations is shaped by individuals' cognitive predispositions, we effectively combine survey measures with economic experiments. Two behavioral experiments are presented in which the timing of online security actions is the critical decision-making factor. The feedback modality in the decision-environment is varied between visual feedback with history (Experiment 1), and temporal feedback without history (Experiment 2). Using psychometric scales, we study the role of individual difference variables, specifically risk propensity and need for cognition. The analysis is based on the data from over 450 participants. We find that risk propensity is not a hindrance in timing tasks. Participants of average risk propensity generally benefit from a reflective disposition (high need for cognition), particularly when visual feedback is given. Overall, participants benefit from need for cognition, however, in the more difficult, temporal-estimation task, this requires familiarity with the task.