Traditionally psychologists who seek to understand stress do so predominantly in laboratory settings. This allows for consistency of measurement and enables researchers to control for some of the possible confounds in their measurements. Currently, stress tasks such as the Trier Social Stress Task represent the gold standard in methodological design for laboratory measurement of stress. Recently, as better wearable technologies have become available, many people are beginning to self-monitor and use these monitors to understand daily stressors in their own lives. This has resulted in a need for the development of methodological approaches that accurately capture these data and daily experiences, and evaluate their accuracy as well as their meaningfulness in understanding psychobiological health and wellbeing outside of the laboratory. We are working to examine the validity of measurements, technological capabilities and the interpretation of large data sets. Our work, comprised of three separate studies, maps patterns of stress reactivity both in the laboratory and in ecological settings, to gain a better understanding of how we can apply psychobiological science and measures in everyday lives.