Driver drowsiness has been implicated as a major causal factor in road accidents. Tools that allow remote monitoring and management of driver fatigue are used in the mining and road transport industries. Increasing drivers’ own awareness of their drowsiness levels using such tools may also reduce risk of accidents. The study examined the effects of real‐time blink‐velocity‐derived drowsiness feedback on driver performance and levels of alertness in a military setting. A sample of 15 Army Reserve personnel (1 female) aged 21–59 (M =41.3, SD =11.1) volunteered to being monitored by an infra‐red oculography‐based Optalert Alertness Monitoring System (OAMS) while they performed their regular driving tasks, including on‐duty tasks and commuting to and from duty, for a continuous period of 4–8 weeks. For approximately half that period, blink‐velocity‐derived Johns Drowsiness Scale (JDS) scores were fed back to the driver in a counterbalanced repeated‐measures design, resulting in a total of 419 driving periods under ‘feedback’ and 385 periods under ‘no‐feedback’ condition. Overall, the provision of real‐time feedback resulted in reduced drowsiness (lower JDS scores) and improved alertness and driving performance ratings. The effect was small and varied across the 24‐h circadian cycle but it remained robust after controlling for time of day and driving task duration. Both the number of JDS peaks counted for each trip and their duration declined in the presence of drowsiness feedback, indicating a dynamic pattern that is consistent with a genuine, entropy‐reducing feedback mechanism (as distinct from random re‐alerting) behind the observed effect. Its mechanisms and practical utility have yet to be fully explored. Direct examination of the alternative, random re‐alerting explanation of this feedback effect is an important step for future research.