Almost all studies of sleepy driving are carried out in driving simulators and with monotonous road conditions (no interaction with other cars). The present study investigated indicators of sleepy driving in a more challenging scenario after a night awake. 17 participants drove a high fidelity moving base driving simulator experiment while sleepiness was monitored physiologically and behaviourally. Short periods of situations of free driving (no other vehicles) alternated with short periods of following another vehicle (car following) with and without the possibility to overtake. The result showed that a night of prior sleep loss increased sleepiness levels at the wheel (eye closure duration and lateral variability) compared to after a night of normal sleep. Blink duration while overtaking was significantly lower compared to the other situations, it was at the same level as after night sleep. Speed when passing a stopped school bus was not significantly affected by sleepiness. However the warning caused a more rapid reduction of speed. In conclusion, a moderately challenging driving contest did not affect sleepiness indicators, but a very challenging one did so (overtaking). This suggests that it is important to monitor the driving situation in field operational tests of sleepy driving.