Shift work requires round-the-clock readiness to perform professional duties, and the workers’ performance highly depends on their sleepiness level, which can be underestimated during a shift. Various factors, including the time of day, can influence sleepiness in shift workers. The objective of this study was to explore the dynamics of sleepiness-related conditions assessed through heart rate variability analysis, starting from the biological evening and continuing in vivo (at home), without the need for artificial alertness support. The participants solely performed regular evening household duties. A total of 32 recordings were collected from the Subjective Sleepiness Dynamics Dataset for analysis. At 8:00 p.m. and every 30 min thereafter, the participants completed cyclic sleepiness scales (the KSS and the SSS) until the time they went to bed, while their heart rate was recorded. The results of the study indicated that during the biological evening, high sleepiness is associated with a ‘stressed’ condition characterized by higher sympathetic activation. Later on, it is associated with a ‘drowsy’ condition characterized by higher parasympathetic activation and a decline in heart rate variability. Our findings provide evidence that the type of condition experienced during high sleepiness depends on the biological time. This should be taken into account when managing work regimes in shift work and developing alertness detectors.