Objective To explore vigilance task performance, cerebral blood flow velocity (CBFV), workload, and stress in a within-subjects, two-session experiment. Background Vigilance, or sustained attention, tasks are often characterized by a decline in operator performance and CBFV with time on task, and high workload and stress. Though performance is known to improve with practice, past research has not included measures of CBFV, stress, and workload in a within-subjects multi-session design, which may also provide insight into ongoing theoretical debate. Method Participants performed a vigilance task on two separate occasions. Performance, CBFV, workload, and self-reported stress were measured. Results Within each session, results were consistent with the vigilance profile found in prior research. Across sessions, performance improved but the time on task decrement remained. Mean CBFV and workload ratings did not differ between sessions, but participants reported significantly less distress, worry, and engagement after session two compared to one. Conclusion Though practice may not disrupt the standard vigilance profile, it may serve to improve overall performance and reduce stress. However, repeated exposure may have negative implications for engagement and mind-wandering. Application It is important to better understand the relationship between experience, performance, physiological response, and self-reported stress and workload in vigilance because real-world environments often require operators to do the same task over many occasions. While performance improvement and reduced distress is an encouraging result, the decline in engagement requires further research. Results across sessions fail to provide support to the mind-wandering theory of vigilance.