The cortisol awakening response (CAR) is a distinct facet of the circadian cortisol rhythm associated with various health conditions and risk factors. It has repeatedly been suggested that the CAR could be a result of the anticipated demands of the upcoming day (stress anticipation) and could support coping with daily life stress. In a sample of 23 healthy participants CARs were assessed on two consecutive days by measures of salivary cortisol upon awakening (S1) and 30 and 45 minutes later, which were aggregated to the area under the curve increase (AUCI). Stress anticipation was assessed immediately after awakening. On the same days, daily life stress and distress were assessed six times per day based on a quasi-randomized design using handheld computers. Associations were tested by day using regression analysis and standard multilevel/mixed effects models for longitudinal data. The CAR AUCI moderated the effect of daily life stress on distress; higher CAR increases were associated with attenuated distress responses to daily life stress on both days (day 1: p = .039; day 2: p = .004) adjusted for age, gender, sleep quality, time of awakening and oral contraceptive use. Lagged-effects and redundancy models showed that this effect was not due to prior-day CAR increases but specific for same day CARs. On day 2, associations between daily life stress and distress were stronger when individuals showed a higher S1 cortisol level, but this effect was similar for S1 on day 1, and the day 2 effect of S1 became non-significant when S1 on day 1 was controlled. No associations were found between stress anticipation and CARs. Findings indicate that the CAR increase is associated with successful coping with same-day daily life stress.